The Breaking
by LadyWallace
Summary: AU to 4x16 "On the Head of a Pin". When Alastair breaks free, he captures Dean and takes him to places unknown, leaving Sam to team up with Castiel in order to find him before it's too late. But other plots are afoot and some of the angels might not want Dean back at all. Dean!Whump Sam is not drinking demon blood. No slash
1. Chapter 1

**A/N: Back writing serious angst again…So I've wanted to write a story with Alastair for a long time because I thought he was a seriously awesome baddie who had a lot of potential and died too soon in my opinion. So I decided that I would make the story an AU of "On the Head of a Pin" 4x16. Pretty much it's a direct tie in with the episode, but Sam is not on demon blood and he's working with Cas instead of Ruby. I really hope you all enjoy the story because I had a really fun time playing with the characters, especially getting to explore some of Castiel's inner struggles. I hope I did justice to his character, this is the first time I've written him from Season 4 and he was a lot different back then, but I hope I was able to portray what I wanted to and still keep him in character. And also I hope my Sam turned out okay too, because I was trying to balance the same angst he had without the added demon blood. Anyway, hope you all enjoy and I look forward to hearing what you think of this!**

 **Rated T for violence and torture, because you kind of have to figure that's going to happen with Alastair. And again, this story is NOT slash.**

 **Disclaimer: I do not own Supernatural; some of the dialogue in this chapter was taken directly from episode 4x16**

The Breaking

A Supernatural Fanfic

Chapter One

 _The First Seal_

Dean's knuckles whitened on the blade that he held in his hand, his back to Alastair before he slowly turned around, forcing a smile onto his face. No, it was impossible; he couldn't have been the one to break the First Seal.

"You're lying," he said, advancing on the trapped demon again.

" _'And it is written that the first seal shall be broken when a righteous man sheds blood in hell,_ '" Alastair quoted with a satisfied, sadistic smile on his face. " _'As he breaks, so shall it break.'"_

Dean's stomach clenched at the words, a chill taking hold of his spine as he forced himself to stay calm, to turn around again before Alastair could see the fear in his eyes. It wasn't true. It couldn't be. If he had actually been the one responsible for starting the freaking apocalypse of all things, then why would the angels have rescued him? It didn't make sense. It couldn't.

"We had to break the first seal before any others; only way to get the dominoes to fall right," Alastair continued, obviously enjoying the fact that he was getting into Dean's head. The hunter couldn't allow that, he knew he had to keep his head, but realized he couldn't. Alastair had hit a sore spot and he just kept digging. Just like when Dean had been on the rack in hell, and truth be told, he still hadn't gotten over that. "Topple the one at the front of the line." He chuckled as Dean still refused to turn around. "When we win," Alastair continued, mocking. "When we bring on the apocalypse and bring this earth down, we'll owe it all to you…Dean Winchester."

Dean swallowed hard, his throat constricting with fear. No, he tried to tell himself. Alastair was lying to get under his skin. Demons lied all the time, he knew this. He forced himself to get his head back in the game but it seemed too late now. He was a mess, he knew it, and he also knew that he couldn't do this. Not now. Maybe a break would help…

"Believe me, son," Alastair said as Dean closed his eyes, trying to calm himself, to ignore the demon. "I wouldn't lie about that. It's kind of a…religious sort of thing with me."

Dean swallowed hard again, opening his eyes. "No," he said with sudden, terrifying conviction. "I don't think you are lying. But even if the demons do win, you won't be there to see it."

He turned around, ready to finish the job despite what the angels wanted, but saw Alastair standing right at his back, out of his chains and grinning. Fear gripped Dean as his mind tried to process this new development past all the other things it was processing at the moment.

"You should talk to your plumber about the pipes," Alastair told him before he swung a fist and slammed it into the side of Dean's head before the hunter could make a move. Dean dropped, the knife clattering from his hand as he sprawled on the floor and Alasdair was on him before he could regain his feet, hand gripping in his shirt, several more severely punishing punches to the head. His vision was already blackening, but Alasdair bent and gripped him by the throat, hauling him up to his feet and slamming his back against the iron trap the demon had previously been chained to. Dean choked, trying to gain at least one breath as he felt his feet leaving the floor, Alastair's face close to his as he continued to choke the life out of him.

"You've got a lot to learn boy," Alastair whispered. "So I'll see back in class bright and early Monday morning." Then he snapped his fingers and Dean completely blacked out.

* * *

 _Castiel had just gone out_ to watch Anna leave, his mind in turmoil over what she had told him. It had only been for a second, but then he felt something….wrong. With trepidation, he entered the abandoned factory once again and pushed through to the room they had been keeping Alastair in, finding it empty, the chains on the demon trap hanging loose and blood spattered outside the ring, which he could tell was human. Dean's.

"No," he said quietly, casting about for some clue, trying to locate Dean but couldn't sense him anywhere. He was either far away, or Alastair was concealing him from the angels.

Castiel felt a foreign darkness inside of him, in the pit of his stomach. Regret? Remorse? Something he wasn't used to feeling, or rather, something he didn't allow himself to feel, especially after he had already been demoted because of his all too human feelings regarding the Winchester brothers. He couldn't afford to let his emotions get away from him again. But yet, this was his fault and he couldn't help but feel remorseful about what had happened. Dean had practically begged him not to make him do this but he had to follow orders.

Everything Anna had just said to him came into sudden sharp focus. Maybe they weren't God's orders after all, maybe… but no, Castiel couldn't afford to think that. He couldn't.

And yet it was something that would eat at him until he was forced to think on it seriously, of that he was certain.

But right now he needed to locate Dean Winchester before Alastair broke him for a second time.

* * *

 _Dean woke blearily, cold_ , sore, and with a certain dark hollowness inside of him that he couldn't remember the reason for. He groaned and shifted against the hard surface he was slumped on, realizing he couldn't move very well. He forced his eyes open, and saw he was lying on the floor of some dark room, likely a basement or something from the cold wetness of it. Memories came flooding back then, of Alastair; Castiel and that douchebag Uriel had made him torture his old master for information. Then something had happened and Alastair somehow managed to get free, beat him up. Then he blacked out, or at least had no memory of what had happened after.

But there was something else. Dean closed his eyes against his aching skull and tried to remember it. And then he did, and wished he hadn't.

 _And it is written that the First Seal shall be broken when a righteous man sheds blood in hell…_

He forced himself to forget again, squeezing his eyes tighter, unable to think about that and worry about his current situation and how to get out of it. Instead he focused on how cold he was and the fact he was in a very bad position. He had been stripped to just his t-shirt and jeans, even his boots and socks had been taken off, his bare feet adding to his chill. His hands were bound tightly in front of him and his legs at the ankles, making it difficult for him to shift around, not to mention the ache in his body. He pulled against the ropes, but only really managed to chafe his wrists.

He was startled by the creak of a heavy door opening at one side of the room. A light was turned on, and he realized that he wasn't in the same room he had been torturing Alastair in as he had thought at first. This room was smaller and there was a table off to one side and a covered cart like the one he had carried the implements to torture Alastair with. Dean swallowed hard, knowing where this was likely going to go as he looked up finally at the man who entered the room.

"Well, well, well, look who's finally awake," Alastair said in his nasally lisp, The wounds he had sustained had healed already and he had changed into clean clothes without bloodstains.

"Why don't you just go back to hell," Dean growled, his voice hoarse from the strangling he had sustained.

Alastair crossed to him and reached down to grab the ropes that bound his wrists, pulling him up and pressing him against the wall.

"We can have just as much fun here as we can there," the demon assured him with a sadistic grin, reaching up to pat Dean's cheek. "I'll just have to be more careful of your mortal body."

Dean tried to struggle, but Alastair held him tightly, getting close to his captive and chuckling as Dean finally turned away. "Oh, come on, my son, tell me you don't miss it? All the good times we had together. My apprentice, and a damn good one too. It was a shame the angels took you away."

"I don't know," Dean replied, finding some of his old bravado. "They ended up making me torture too, after all. Go figure, right? But I don't know why you want me. They'll just find me eventually, and then kill you. Trust me, it's not easy to hide from Heaven's hit squad."

"I've warded the place against the feathered annoyances," Alastair assured him with a grin. "We won't be interrupted, don't worry."

"What do you want, Alastair? What can I tell you that you don't already know?"

"Oh, Dean," Alastair chuckled and shook his head. "This isn't about information. This is just for old time's sake. A little…reunion, so to speak." He reached into his pocket and pulled out a razor, always his favorite implement, and Dean suddenly felt weak in the knees. "Remember our old friend, Dean? She remembers you. We're going to have, oh, so much fun."

* * *

 _Sam paced the hotel room_ , anxiously biting his knuckles and trying to figure out what the hell he was going to do. He hated sitting idle, but there was nothing he could do until he knew…well… _something._ Anything at all, really, would do. The angels had just whisked Dean off to parts unknown without a by your leave, and to what purpose? To act as their torturer? Obviously they were too good to dirty their own hands so they had to force the job upon his brother who was trying to forget what he had gone through in hell, what he had done, because apparently that was all Dean was good for anymore. Sam was beyond furious about the whole situation, and wished he could do something, anything, to at least find out where they had taken Dean.

"Castiel!" he cried finally, thinking maybe praying to the angel would get his attention. He had seemed a little more lenient than the others, even though he seemed to be under Uriel's thumb at the moment for whatever reason. "Castiel, answer me, you bastard! I want to know where you took my brother!" After nearly half an hour shouting uselessly, he finally ended with, "At least tell me when you'll bring him back!"

He slumped onto the end of one of the grungy hotel beds and lowered his head into his hands as he sighed tiredly. He didn't like anything about this situation. The angels obviously had some plan for Dean but they weren't willing to tell him about it, and on top of that, they didn't seem to see, or care, that Dean was in a bad place right now. Sam knew his brother better than anyone, and he saw the damage hell had done to Dean. His heart still ached when he remembered his brother's strangled confession about breaking in hell, torturing souls in his place for Alastair. It had broken him in more ways than one, and Dean was only half the man he had been before. Sam had been trying to put his brother back together again, but the angels and their crusade with these stupid seals weren't helping. They were only making it worse, especially if they kept making Dean do these kinds of things. They may as well throw him back into hell like they threatened.

Sam started to call to Castiel again, when the angel suddenly appeared in the room, startling him.

"Oh, now you show up?" he demanded, standing and glaring down at the shorter figure. "I've been calling for hours!"

"I heard," Castiel told him blandly. "I couldn't come."

"Not even to answer my questions? Where's Dean?"

"Sam I need you to listen to me carefully," Castiel said slowly, but Sam cut him off, too angry to care about any excuse the angel would make.

"You know what, Cas? No, you listen to me. You may not be able to see it, but Dean is broken, I don't know what exactly is going on with him, but he can't do things like he used to. Whatever happened to him in hell broke him and if you keep forcing him to do little tasks for you like torture people, especially a demon who will drudge up the worst memories possible for him, I will take him away and hide him where you will _never_ find him. Good luck stopping your apocalypse then, if we're really that important to you."

Castiel stepped closer to Sam, his gaze intent upon the younger Winchester, something in his stance finally making Sam go quiet. "I am following orders like everyone else, Sam, none of us have the luxury to sit this out whether we're broken or dying or otherwise. This is the end of the world as you know it that we are talking about. I wouldn't have had him do this if it hadn't been necessary, especially if I had known…" he stopped suddenly, casting his eyes away from Sam.

"What happened?" the hunter demanded, not liking the look on the angel's face or the way he hesitated. "Did something happen to Dean? Cas?"

The angel faced him again. "Our trap was not as secure as we thought. Alastair managed to free himself during the interrogation."

Icy coldness spread in Sam's stomach. He reached out and gripped the lapels of Castiel's trench coat, shaking him slightly. "What happened, Castiel? Is Dean…" he couldn't bring himself to say the word.

"He's still alive as far as we know," Castiel told him. "But he's been taken by Alastair and it is imperative that we find him as soon as possible." He barely blinked when Sam slammed him back against the wall, his hands trembling where they were still clutched in the coat.

"You're saying he's with the one person who could destroy him completely? When were you planning on telling me?"

Castiel gripped Sam's wrists and forced his hands to let go as he drew himself up to his full height, staring the young man down. "I'm here now, because I knew you would want to and deserved to know what happened, and also tell you that we are doing what we can to find him right now. Alastair seems to be concealing him from us. Now you will let me go if you wish your brother to be found before Alastair does too much damage to him."

"Wait a second," Sam growled, gripping Castiel's sleeve as he turned away, as if that would actually stop the angel from leaving if he wanted to, but thankfully Cas seemed to be willing to hear him out. "I'm going with you, or I will never let you see Dean again even if it means the world will come to an end, do you understand me? You got him into this mess, and I'm going to make sure you get him out."

Castiel glared at Sam so darkly that the younger Winchester actually took a step back. "You are experiencing high anxiety, so I will forgive your impudence. But I would prefer you show me some manner of respect since I am doing what I can to find your brother. If for no other reason than to practice when around the other angels who will not take such insults in stride."

Sam swallowed hard; more in fear of a refusal to let him come than of his own life coming over him. "Please," he said more quietly. "I can't just sit here and do nothing. Besides, if he _is_ warded against angels, you might need a human to get him out."

Castiel was silent then nodded. "That is true. Besides, I know you will not rest until your brother is safe, so I shall let you come so you won't get in our way and impair the operation, but only if you agree to follow my orders."

Sam clenched his jaw but nodded, knowing he had no other choice. "Fine."

Castiel furrowed his brow, but seemed to see the hunter's conviction, because he nodded back once. "Then we have no time to waste."

* * *

 **Hope you liked the start :) I have a sort of prequel one-shot that goes along with this story that I hope to post later this week, and I hope you'll read it because it will give you more insight into Castiel's inner struggles. Please leave a review if you are so inclined :)**


	2. Chapter 2

**Hey everyone! Back with chapter two! Thanks so much for all the reviews and follows, I'm happy people seem to be liking this and I hope you continue to do so :) Also, I know I said I was going to get a one shot up that goes along with this story, and I still will, promise, I just didn't have time to finish it this week, but *hopefully* I'm planning on posting it either thursday or friday so keep a look out :)**

 **Warning: This chapter starts in with the torture, but only really in the last part, and a little in the flashback but it's mostly monologging.**

 **By the way, updates will be posted every monday, in case you're wondering.**

Chapter Two

"Well, isn't this nice; just like old times. Hm, Dean?"

Dean tested the restraints that held him to the metal table Alastair had moved him to as the demon prepared for whatever he had planned, fiddling with something on the cart behind Dean's head where he couldn't quite twist to see. He was chained hand and foot, his arms up by either side of his head, and there wasn't a lot of give. It wasn't looking good for escape, and even if he were somehow able to get free of the restraints, where would he go? He had no idea where he was, or even what state he was in. What country, to be honest. Alastair could have drug him to Antarctica for all he knew though that was a little extreme. All he knew was that he was doomed, because he was not the cocky devil-may-care screw-the-world-I-died-for-my-brother hothead who had gone to hell in the first place. No. Alastair had broken him once, and he was going to do it again given the time, Dean knew it. And given the angel warding, he was probably going to have the time. Not that Dean wanted Charlie's Angels coming to his rescue, but if he could find a get out of jail free card, he wasn't exactly going to complain. He still held out hope that Cas might not be a total dick, even though he sure acted like it half the time, he had at least looked somewhat sorry when they had dragged Dean off to play interrogation. Now that Uriel was calling the shots though, Dean didn't know what he could expect. He knew the angel didn't like him—yeah, okay, it had probably been partly his fault,—but maybe he was still valuable enough for them to at least attempt a rescue. And maybe, just maybe, if Cas had indeed come to 'care' about him causing him to be knocked down in rank (not that he was feeling the love exactly) then he might chance a little healthy rebellion to get Dean out of here under Uriel's nose. Especially if Sam had anything to do with it, because Dean knew his brother well enough to know that by now, if he knew what had gone down, he would be royally pissed and Castiel was going to be the first one to bear the brunt of it.

But as his musings went on, Alastair had finished whatever he was doing and wheeled the cart over next to Dean, humming tunelessly. Dean pretended nonchalance, but he was really fighting back panic, his heart pounding so loud Alastair must have been able to hear it. Maybe it was PTSD or something, maybe it was just rational thinking, but Dean felt like he might have a full-blown panic attack any minute and that was not like him. Not before he had gone to hell anyway. But he knew he was different and the too much drinking and too little sleep wasn't helping at all, likely only making it worse. But there was nothing he could do about that now, so instead he put his shield in place as well as he could and smirked up at Alastair. "I will admit, I was starting to feel stood up, Alastair."

"Ah, there's my boy," Alastair said with a pleased chuckle, checking Dean's restraints to make sure they were sound. "Do you remember the first time we met, Dean? I didn't really know what to expect, but I must say you really did impress me. It took a long time before I could get you to really scream and even longer to get you to stop with your snarky attitude. You were always so stubborn."

"Yeah, well, I like to make 'em work for it," Dean told him, proud when his voice didn't waver. This was at least familiar. The pre-torturing taunts/rejoinders before Alastair would sever his vocal chords, or maybe cut out his tongue, or neither; whatever pleased him most on a certain day.

Alastair tsked. "I see you haven't changed. That's good, Dean, I was hoping you weren't a blubbery pile of anxiety and self-pity. You were always better when you weren't wallowing in self-hatred and miserable resignation. I'm not lying when I say you were one of my best students. Quick learner, and, oh, so determined to please. Anything not to go back on that rack, eh, Dean?"

Dean looked away from him as Alastair shot a meaningful look that was meant to drudge up more of that self-hatred. The demon chuckled and shook his head. "Anyhoo…" he whisked the sheet off the cart and Dean refused to be swayed by the various implements sitting there. It's not like he hadn't been there before a thousand times. Besides, he knew well enough the Alastair had always favored the razor most. "I was…disappointed when they took you away, Dean. Even more so that you went with them. I wonder why they bothered, really." There was the razor in his hand now. Always gleaming and sharp even among the usually rusty implements they used in hell. "I mean, you'd already broken the Seal, there was really no hope after that. What use was little old Dean Winchester to the angels?"

Dean forced a chuckle out of his dry throat. "Tell you what. If you find out, do me a favor and let me know."

"Not very forthcoming are they?" Alastair asked, cocking his head to one side. "Why did you go with them? I thought we had a good time. You had a lot of promise, Dean. Better than the others and believe me, that's high praise coming from me."

Dean forced himself to calm down. There was no way he was going to let Alastair get to him yet. "I don't remember everything, especially not them angel-lifting me out. Besides I don't think I really would have had a choice."

"But would you have stayed if you did?" The loaded question. An easy one, though.

Dean looked up at Alastair and met his pale eyes. "No."

"Oh, that's right. Dear little Sammy, can't be without his big brother," Alastair curled his lip. "You were always so sentimental, Dean. I could have helped you with that given more time. But, oh well. I suppose we should get down to business then. I've left you waiting long enough. Now." The razor touched the center of Dean's chest, wickedly sharp even through the fabric of his t-shirt, as it traveled slowly down his body, causing his breath to stop as memories were brought back. Same as in the nightmares he had been having, but this was no nightmare. "I'm wondering how long it's going to take you to scream this time."

* * *

 _Dean hadn't really known what to expect, sure he knew hell meant torture, and he figured it was going to be bad; eternal torment, fires of hell and all that. But waking up strung by hooks in a vast darkness after the vivid memories of getting torn apart by hellhounds to his brother's screams, that threw him for a loop, he had to admit. And the pain was odd, because it was so real and mortal, going so deep and literally into his soul, and yet he knew it wasn't going to kill him._

 _But that wasn't anywhere near what he experienced for the first time on Alastair's rack, when he was finally retrieved from his suspension and dragged to deeper parts of hell, where screams emanated, terrible unearthly sounds that he couldn't imagine coming from a human throat. It was then he had decided that he was never going to allow them to make him scream like that._

 _But then there was Alastair._

 _The demons had left him on the rack, chained up so that he couldn't move an inch and then Alastair came._

 _"Well, well, well, Dean Winchester in the flesh…or, something like that," the demon said with glee. "I've been waiting to meet you." He gave a mocking bow. "Alastair, chief interrogator down here. I've been assigned specially to break you since I know the breed." His chuckle chilled Dean to his core._

 _"What do you mean?"_

 _"Who do you think was in charge of your daddy when he was still down here?"_

 _Dean, horrified at the news and angry at the fear that gripped him, jerked in his chains and growled at the demon. "You son of a bitch, I'll kill you."_

 _"That's good, Dean, you keep that attitude up, you'll last longer," Alastair told him, before reaching over to a covered tray set up by the rack. He pulled the cloth aside and that was when Dean first saw the razor that he would become so intimately acquainted with among other things. "Why don't we play a little game?" Alastair said, studying the small, deadly looking blade intently. "Let's see if you can last as long as your daddy did without breaking." And then he turned and started working on Dean._

 _And it went on like that for days and days, carving, ripping, and tearing Dean apart over and over again until his resolve crumbled and he could no longer hold in the screams that he had fought so hard to keep in. Had refused to stoop to. That pleased Alasdair so much he stopped his tortures and smiled at Dean, patting his cheek with a bloodstained hand._

 _"There we go, Deano, That's what I'm looking for."_

 _And that was the first day that Alasdair had given him the offer to get off the rack, and the first time Dean refused him. But that was just the beginning, and as much pain as he had been in then, it was nothing compared to what was still in store._

* * *

 _Sam and Castiel drove in the Impala_ , Sam refusing the leave the car since the warehouse they had been keeping Alastair in was only a few hours' drive away. Castiel had insisted on going back there to see if they could find any evidence of where Alastair had gone and Sam had grudgingly agreed that it was likely the best course of action, and really the only thing they could do at that moment since they still had no indication of where Dean might be.

"It is strange," Castiel said after a long silence, giving Sam a bit of a start.

"What is?" he grunted, not really wanting to talk, especially not to the angel who had lost his brother.

"This automobile. You humans use them to get around quickly, and yet, compared to how I travel it is very slow and cumbersome. How do you orient yourselves while you're in them? It seems that it would be very confining while trying to figure out what direction you need to go."

Sam huffed, annoyed. Was the angel really trying to make small talk right now? But then, he decided he probably was genuinely curious. After all, Castiel had likely never ridden in a car before.

"It's not really hard, especially when you've never known any different," Sam said grudgingly. "I mean, you just follow the roads and maps and stuff."

"Unlike some of my brothers and sisters I was always amazed by you humans' ability to create such intricate pieces of engineering. I remember when you still dwelt in caves and first discovered the uses of fire. You have come a long way since then."

Sam couldn't help a short laugh. "Yeah, I guess it would be strange to see everything that's changed."

"I find it fascinating," Castiel told him sincerely. "And it makes me realize the importance of saving humanity."

"Well, right now, I just care about saving my brother," Sam replied bluntly.

Castiel looked over at him. "You and Dean have a very strong bond, even for brothers. It is rare, and unlike some of my comrades, I do not see that as a bad thing. I think it makes you stronger, and it is inspiring."

"He raised me, practically," Sam said quietly, not really wanting to talk about this with the angel.

"I know. Dean Winchester is a good man," Castiel said. "But he needs to learn his place as well. You both do. I know it is a hard concept to grasp, especially when you're used to independence, but there are bigger things that need to be done, and they cannot be accomplished without the help of you and especially your brother."

Sam's hand gripped the steering wheel angrily. "So we're just your puppets? Why don't you try telling me what you really want Dean for? Because I know it's not just going on wild goose chases for seals and playing interrogator so you don't have to get your hands dirty."

Castiel shifted awkwardly in the seat. "You will know when it is time, Sam, but right now, we're here. The warehouse is up ahead."

Knowing he wasn't going to get anything else out of the angel at that time, Sam huffed and pulled off the road to park in front of the warehouse. He followed Castiel inside and through to an inner room where he saw a demon trap and an iron pentacle with loose chains hanging from it. He stopped when he saw the cart of holy water and salt and blades and syringes and whatever else Dean might have been using to torture Alastair. He swallowed hard. This was not a part of his brother he could easily imagine. Sure, they had done their share of 'rough questioning' but it had rarely gone beyond fists, and holy water when it came to demons and such. Never the methodical, sadistic type of torture that needed implements and creativity. That was not the Dean Sam knew, and it made him sad and maybe a little scared deep inside, because he knew that the Dean that Castiel had rescued from hell was not completely the Dean Sam had known his whole life. And he was just going to have to get used to it, because going through those kinds of things changed people forever. It wasn't just something you could put a bandage on or drink away at night, though Dean seemed to be doing his best with the last one. But Sam shoved those thoughts aside for the moment. He knew that no matter what had happened to his brother, what Dean had done, he would still be his big brother, and Sam was going to do everything he could to get Dean back as well as he was able, no matter the consequences. And he certainly wasn't going to let the angels and their crusade get in the way of that.

Sam took a deep breath and turned to where Castiel was inspecting the trap. He carefully stepped over some blood spatter on the floor, hoping it wasn't all Dean's, and frowned at the trap.

"He got out of this?"

"It is inconceivable, I know," Castiel replied, frowning. "It is old Enochian, and should have held. I made it myself."

Sam held back a biting reply about the angel's crappy work, seeing that even though Castiel didn't show much emotion at all, he was troubled by the events. And even if he could never care for Dean like Sam did, he _had_ been the one to risk his life or whatever getting his brother out of hell, and if for nothing else but for the waste it would be to lose Dean now, Sam knew he could trust the angel. Even if he didn't like it. Besides, studying the trap, he could tell that it had been put together well, way more heavy duty than their typical demon traps, and should have held.

A small puddle of water on the floor caught Sam's attention and he swiftly knelt to see it more closely. His jaw tightened as he saw the sigils that had been drawn in chalk on the floor washed away in one spot.

"Hey, look at this," he called and soon the angel was crouching down next to him.

"I…don't understand," Castiel said, frowning and looking up. "I checked the pipes, they were secure."

Sam stood up and inspected the pipes himself, frowning deeper as he ran his fingers over the seam. There was no rust, no wetness from the seam directly above the damaged part of the trap. He grasped the screw and twisted with no luck.

"Let me," Castiel said and reached up to give it a sharp turn, causing a small trail of water to trickle down before Sam told him to close it again.

"This must be how Alastair escaped," Castiel said. "But I don't understand, I checked to make sure everything was secure. This should not have happened."

"Well it did," Sam replied shortly. "And now he has Dean. More importantly, this wasn't an accident. It was done deliberately."

Castiel opened his mouth, then closed it again. "I see that, but who?"

"Could Alastair have opened the pipes?"

The angel shook his head firmly. "No, it would be impossible. He was chained securely and the trap kept his powers at bay."

"Well, Dean obviously wouldn't have done it, so that only leaves one possibility." Sam turned to Castiel grimly. "It looks like you might have a traitor in your midst."

* * *

" _Come on, Dean, you don't_ seem to be enjoying this at all. Haven't you missed it as much as I have? You have to admit that it's only fair; turnabout and all that, that little session we had earlier—you are good Dean, but you're getting rusty. Too much time off. Thought I'd give you a little lesson to remind you how it's really done. Where's all the threats and snark? You can't tell me I've broken you already."

Dean ground his teeth in pain, his body on fire from the shallow cuts Alastair had sliced up his arms and legs, currently working on the soles of his feet. "Maybe I'm just too bored to give a crap," he gritted out, his toes curling in defense of the cold blade against his bare feet, trying not to think about how bad that was going to hurt to walk on later—if he ever got out of there, that is.

Alastair straightened up and moved to stand by his head again, replacing the razor on the table as he took up a rag and slowly wiped blood from his hands. "You're right, this is a little tame after what we've been through together. Especially after what you've done yourself—always imaginative, I can't help but give you points for creativity. Our little session earlier was certainly…educational."

Dean managed a cocky smile. "What can I say, I like to employ my natural sense of style."

"To be honest, I wasn't sure you would have the…conviction to actually turn on your old master. I must say it did surprise and impress me. Made me proud even."

"Trust me, it was easy to slice you up. A privilege really," Dean smirked.

"It is a bit difficult up here, though, you have to admit, especially for you. I can't just throw on the holy water and watch you burn. I have to preserve that body of yours—can't have you checking out too soon. I'll take a page from your book and try to be a little more…thoughtful." He took the bloodied rag and gripped Dean's jaw, forcing his mouth open. Dean struggled but the cloth was shoved into his mouth and Alastair held his head still as he grabbed a jug of water from the table. "A little bit of waterboarding never goes amiss." And he poured it onto the rag in Dean's mouth, making him gag and choke. He pulled against the restraints and Alastair smiled, pleased as he finally stopped pouring the water and gave Dean a breather, the hunter spluttering past the rag, sucking air through his nose and choking on the water still in his mouth.

"Thought you needed a cool down," Alastair informed him before he repeated the torture several more times until the jug of water was empty and he set it aside, pulling the gag from Dean's mouth. The hunter choked up some water, his body racking with coughs before he settled back, shuddering and breathing heavily.

"I always thought waterboarding was lame," Dean mumbled.

Alastair nodded slowly. "Perhaps something a little… hotter then?" He bent to the lower part of the cart and pulled up a small iron brazier looking thing, which he proceeded to light, then pulled out a fire poker as the coals glowed warmly. "Reminds me of home sweet home," Alastair said, smiling at Dean as he turned the poker in the coals until it was glowing red hot. "You always did hate the burning, didn't you Dean? Reminds you of how mommy dearest died, doesn't it?"

Dean ignored the jibe and tensed as the brand was pressed against his ribs, unable to help the strangled shout that came out.

Alastair hummed in satisfaction and closed his eyes as he breathed deeply, inhaling the rank odor of burned fabric and flesh. "Oh, yes that does bring me back."


	3. Chapter 3

**Back with chapter three! Thanks again for everyone who has read this already, I'm glad to see you're enjoying it!**

 **If you didn't see it, I finally posted the companion/prequel one shot to this story "When You Wake" so please go check that out, because I think you'll appreciate how I'm trying to portray Cas' character in this story more, if you read that one :)**

 **Warnings: This chapter contains another mildly gruesome torture scene. Sorry in advance, let's all give Dean a hug.**

Chapter Three

"No, I…no," Castiel shook his head. "The angels would not betray our mission."

Sam slammed his hand down on the cartload of torture implements, making it rattle. "I don't give a crap about your mission right now, not while Dean is missing and likely being tortured by the demon _you_ failed to contain. Why don't you grow up and realize what the world is really like for a change?"

Castiel swung around to face Sam, a hand gripping into the hunter's jacket like a vice. "And what do you know of the world, boy? You are an infant compared to me, not even that. I went to hell to retrieve your brother at great personal cost. I lost brothers and sisters I loved on that mission, and you will show me some respect for that if nothing else."

Sam swallowed, fear gripping him as he looked into Castiel's eyes, but he couldn't help being angry. Could Castiel really not grasp the idea that the angels might not be all harps and halos? But he knew Cas wasn't going to see the truth, whatever that might be, without proof, and Sam couldn't really blame him for that either. If someone said the same about his family, he would get defensive as well. He fought to unclench his fists and finally managed to relax. The moment he did so, Castiel released him with a small shove.

"All the same, I will make inquiries," the angel said, surprising Sam. "I will contact the others involved in the search and…"

He stopped as flapping was heard and Uriel appeared in the room with them, bringing Sam instantly on guard.

"Uriel, I was just about to contact you," Castiel said.

"What is he doing here, Castiel?" the angel asked, looking at Sam like he was a bad smell.

"I brought him to help. If Alastair has warded his hiding place against us, he may be needed."

"He will only get in the way with his foolish human emotions. But then, you would give in to his pleas for that, wouldn't you?" The disgust in Uriel's voice suddenly made Sam sorry for Castiel. He may not be friendly with the angel, but at least Cas seemed to be on his side. And there was just something about Uriel that he didn't like. Didn't trust him at all.

"I believed Sam would be an asset," Castiel said firmly, though Sam could tell he was not completely unfazed by his comrade's insinuations. He remembered then that Castiel had been knocked down in rank for 'caring about the humans in his charge'. What the hell was that about? What did it even mean? Was it a crime to care?

"The Winchester boy will only get in the way," Uriel said.

"He promised to follow orders," Castiel insisted.

Uriel smirked. "Promised to the angel who has trouble following them himself?" He shook his head, gaze shifting between the two standing before him.

"This is not about me, Uriel, this is about finding Dean," Castiel ground out. "I know you enjoy flaunting your new position over me, but we need to keep to our orders. Sam and I found evidence of foul play. The trap was compromised by a leaky pipe."

Uriel laughed. "A leaky pipe? Oh, that one will hold in court. Are you so sure that Dean Winchester didn't simply run off willingly with his old master?"

"You son of a bitch, how dare you?" Sam snarled, reaching for his gun and starting toward the angel who just stood and laughed at him as Castiel slammed an arm into Sam's chest and forced him back, keeping a firm grip on his shoulder.

"Dean didn't go with Alastair willingly, that I am sure of," Castiel told him. "But we need to find out who was responsible for this. Uriel, it is possible that there is a traitor among us. I spoke with Anna earlier…"

"Anna?" Uriel demanded. "If there is a traitor it is she. She probably did this to turn us against each other. In fact, she probably hired the demons to kill our brothers and sisters to begin with. If she said there was a traitor, it is all lies."

"Still, do you not think that we should look into it?" Castiel continued earnestly. "If it could save more angels from death, then…"

"No, Castiel, we will not make inquiries among our own, especially when we know who the traitor really is." He looked at Sam like it was all his fault. "Oh yes, and I forgot why I came to find you. You are no longer going to help us in the search for Dean Winchester. You are to report back to heaven immediately for further orders."

Castiel frowned, his mouth open in surprise. "But Dean is my charge, I cannot just abandon him now…"

"You're being reassigned," Uriel stated with a sadistic glee in his eyes. "You had best go now before you are forced."

Castiel stared at Uriel for another long moment before he strode purposefully out of the warehouse, Sam hot on his heels, trying to figure out what just happened.

"Cas, hey!" he shouted, grabbing Castiel's shoulder.

The angel spun around. "Sam, I do not have time for this."

"Woah, you're not just going to leave, are you?" Sam demanded. "You're going to let that asshole tell you what to do? I need your help finding Dean, I can't do it alone with no leads, and I sure as hell am not going to trust the other angels to find him!"

"I don't have a choice," Castiel ground out, raising his voice. "If I don't follow my orders I won't be in any position to help you or Dean. Trust me, I don't like it any more than you do, but I have orders to follow, and so do you, if you know what's good for you."

"So you're giving up?" Sam demanded. "After you went to _hell_ for him? You just got done telling me about your sacrifices, don't you dare turn it around and say it doesn't matter. That _Dean_ doesn't matter. Because I can see through you, Cas, and I know that even if you pretend to be the good little soldier, you are thinking about the traitor, and you know it's not Anna. Look, go if you have to, I can't stop you. But do me a favor and _think_ about it. Think about what makes sense, and think for yourself for once. That's all I ask."

Castiel looked like he was going to say something and then hung his head slightly. "I'm sorry, Sam. I wish I could help." And then he disappeared.

"Dammit!" Sam shouted at the empty space in front of him, alone once again and no closer to finding where Dean was. He got back into the Impala and drove back to his hotel unable to do anything else.

* * *

 _Alastair gave Dean a breather_ after he had finished with the brand. Dean closed his eyes against the pain singing through his body during those moments of reprieve, breathing shallowly, and wincing every time the still intact parts of his shirt grazed against the burns on his chest and abdomen with every inhalation. The smell of his own burning flesh was still fresh in his nostrils and made him want to vomit. If he'd had any food in his stomach he probably would have, but he hadn't eaten in over twenty-four hours and his stomach was an angry hard knot in his belly.

He tensed as he heard Alastair's footsteps come into the room again from wherever he had been and opened his eyes, steeling himself, and forcing some energy into his system. At least enough to not give Alastair the satisfaction of seeing his suffering.

The demon chuckled and shook his head. "There're those pretty, defiant green eyes of yours. I forgot how good you were at hiding the pain, Dean. Funny how some people have no trouble screaming and whining and others simply refuse." He dug his finger into a nasty burn on the underside of Dean's arm and the hunter gritted his teeth, grunting in the back of his throat.

"So, Dean, are you ready for round two?"

Dean gave a breathless chuckle. "Go screw yourself."

Alastair tsked fondly, taking up his razor again. "There's my boy. I was worried you would start fading away already. You were giving me such nice screams during the burning session—not quite what I was looking for, mind, but closer." He traced the blade down Dean's cheek, and the hunter flinched away, snarling. "Oh, don't be like that," Alastair chided, bending down and turning Dean's face toward him. "That's no way to treat your old master, is it? You know, Dean, once upon a time, when you were my best student, I was willing to offer you more than just my mentorship. I could have been like a father to you—even my dark, twisted soul became rather fond of you." He chuckled, resting the blade in the hollow of Dean's throat. "I was certainly more willing to offer encouragement and praise than your daddy."

"You shut your mouth," Dean snarled. "You were _never_ like my father, don't you dare mention him."

"Touched a sore point, did I?" Alastair asked with a mocking brow raised. "Never did care what I said about you, but when it comes to daddy and mommy…and dear baby Sammy…now, that's the one that always gets you. Do you know how easy it would be to go find him and bring him here? I bet you he's out looking for you right now, just waiting to fall into my trap. How long do you think it would take Sammy to break, Deano? Do you think he would last as long as you? Longer? Or would he give in instantly?"

"Shut up," Dean warned, trying not to show how badly Alastair was getting to him.

Alastair traced the blade down his chest slowly until it reached the amulet that resting on his breastbone, tapping it gently. "I can just see him, trying oh, so hard, to be brave for you, his big brother, who would be watching while I tore him apart. Showed you his insides." He slit the bottom of Dean's shirt and ripped it to expose his stomach. "Would he beg for you to save him, Dean? Just like you begged him when you first got to hell?"

"Shut the hell up!" Dean snarled, jerking up as far as the restraints would let him, which was only a few inches off the table. Alastair chuckled, forcing him flat with the sharp blade against his stomach.

"Another sore spot," Alastair commented, pleased with himself. "You see, you seem to forget, Dean," he traced the blade to Dean's left hip and sunk it in all the way, making him gasp in shock, "I know you, inside and out—literally, as you well know. I know what makes you tick, I know what keeps you up at night, and I know what brings you to your lowest and breaks you into pieces. For instance," he drew the blade out, and Dean shuddered, whimpering quietly, "I know you enjoyed torturing for me. But you also hated yourself for it. That's you all over, Dean. So much self-hatred, and you wonder how I broke you so easily. You wonder why the angels are able to control you. You're just a grunt, a lost little boy who needs someone to answer to or you don't know what to do."

"That's crap," Dean said hoarsely, his voice hitching as Alastair sunk the blade into his lower belly.

"You keep telling yourself that, Dean," Alastair said resignedly before he looked back up at Dean. "Of course, you can't really blame yourself, Dean, it's really all because of your daddy. The way he treated you like a little soldier and never gave you any slack." He shook his head in mock sadness. "Poor little Dean. Never got the childhood he deserved."

Dean wanted to reply but didn't. Why bother? It wasn't going to make any difference. Instead he choked out a hitching gasp as the blade found another tender spot. Alastair continued.

"Did you know there's plenty of places you can sink a blade into someone without doing permanent damage?"

"Fascinating," Dean snarked.

"I'm glad you think so, we're going to put them all to the test," Alastair told him.

"Okay, you got to talk smack, tell me about myself—nothing I don't already know, believe me," Dean said, gritting his teeth a little as Alastair's blade traced across his lower stomach, making him tense and squirm. "So it's your turn to tell me something. Why didn't you just kill me back there? Why risk the angels catching up to you and doing you in?"

Alastair chuckled, pausing in his work so he could look up at Dean. "What fun would that have been? Besides, the angels aren't going to find me. We have an…understanding, shall we say?"

Dean groaned as the blade dug into a particularly tender spot under his ribs. "What do you mean, 'an understanding'?"

"Let's just say one of your feathered friends isn't all he pretends to be," Alastair told him, slowly tracing the blade over the point of Dean's hipbone and watching the blood seep into the waistband of his jeans.

"Cas?" Dean had to ask, wincing, hoping it wasn't true, not that he really cared, but still, Cas had rescued him from hell, he hoped he could at least trust him.

Alastair laughed as if that were funny. "That stupid pigeon didn't even want you near me again—I got to do a little eavesdropping before they went to get you—he thinks of himself as your guardian or some nonsense. No." He stopped carving for a moment, moving up the table to look Dean in the eye again. "It's not your precious Castiel. That's all you need to know. Now, enough chit chat, let's really get down to business. I get the feeling I'm not going deep enough." He ripped Dean's shirt up the rest of the way, fully exposing his torso and pushing the ripped pieces aside. He picked up the amulet to Dean's steely gaze, fingering it with amusement. "Always were fond of this, weren't you?" He yanked it over Dean's head to the Winchester's protest.

"No, you give that back!" he snarled.

"You'll have no need of it before long," Alastair told him, throwing it onto the cart. "I'll send it to your brother when my condolences when I'm through with your sorry carcass." He turned back to his captive and his eye caught the handprint scar Castiel had left on Dean's shoulder when he rescued him. Alastair flicked the torn fabric of Dean's t-shirt away from it and shook his head mockingly.

"I just have to wonder, Dean, why they went through so much trouble to get you out when you were only going to die by my hand up here. It really is ironic, isn't it?" And then he took his blade to Dean with renewed enthusiasm and this time, Dean had an even harder time holding back his screams.

* * *

 _Sam was back in the motel room_ again. It was almost after dawn now, and he hadn't slept all night even though he had been exhausted when he had gotten back from that hunt with Dean what seemed like days ago but hadn't even been twenty-four hours. He didn't know what to do. He had called Bobby and told him about the predicament. As was typical, Bobby was all kinds of angry, but he promised he'd look into locating spells Sam might be able to do to find at least a location Dean was being kept. But until then he could do nothing but sit there and worry about Dean and think about how pissed at Castiel he was.

For a minute, he had actually thought the angel cared enough to help him, and had actually felt sorry for him when Uriel was smirking and gloating about his new rank. But that had all diminished after Castiel had run back home like he was afraid of a whipping or something if he didn't and totally disregarded everything he and Sam had talked about. It made him so angry. He just couldn't understand why Castiel would risk everything to get Dean out of hell only to abandon him now when they were only going up against one demon.

He was just working on making a pot of coffee when he heard the flapping of wings and spun around to see Castiel standing behind him. He slammed the coffee pot down on the counter and glowered at the angel. "You have a lot of nerve showing up here."

"I am trying to help you. And Dean," Castiel told him then seemed to deflate in a way Sam had never seen him do. "I am truly sorry about last night, Sam. But you have to understand that these are difficult times for all of us, especially in heaven right now. The pressure put on our warriors fighting to save the seals has taken its toll. I have lost many brothers and sisters in the field in the past few weeks to Lilith and her demons, and now more of us are being killed, or rather murdered, by an unknown perpetrator. We do not have the _luxury_ for any sentiments that might arise, no matter the circumstance."

Sam snorted. "Sentiments? You mean simply caring enough about someone to save them when they're, I don't know, in danger of _dying_? Do you think you can manage that?"

Castiel narrowed his eyes at the younger Winchester but didn't comment on his sarcastic tone. "I am here because I care, Sam. I'm here to help you find your brother."

Sam was slightly surprised at the news. "But I thought you were reassigned?"

"It seems Uriel was a bit premature," Castiel explained. "I argued my case and convinced them to allow me to continue in the search for Dean, though with the warning that if there were any…concerns…about my loyalty afterward, I would be reassigned permanently."

Sam stared at the angel for a long time, trying to process this. Okay, so maybe he had misjudged Castiel after all. The angel cocked his head, frowning.

"Is everything alright?" he asked hesitantly.

Sam shook himself. "Yeah, sorry, I just…you actually do care. You're not like the others."

"I feel you judge my comrades poorly, and I apologize that Uriel is likely not the best example." A small smile. "But the truth is, Sam, that I know there is something going on in heaven. Times like this truly test loyalties, and I fear the seed of dissent has made its way into our ranks. I may not agree with Anna and her reasons for falling, but I am not inclined to believe she is behind any of this either. In a way, I do understand why she rebelled. It is… wearing seeing your family tear itself apart." He looked down then, before turning back to meet Sam's eyes. "Perhaps that is why I understand you and Dean a bit better than some. Dean, and in association, you, have been my charges for longer than you likely realize. I cannot stop my duty now, especially when my help is truly needed."

Sam gave him a small nod, feeling a new blooming respect inside of him for the angel. "Thank you."

"I only hope that in recovering Dean, we may also find out who the traitor is."

"Me too," Sam agreed sincerely. "So, what do we have to do?"

* * *

 **They're on their way to the rescue :) Again, check out "When You Wake" if you get the chance, and I'll see you next week with the next update :)**


	4. Chapter 4

**We're back! Thanks as always to everyone who has read and reviewed so far, I always love to hear what you think :)**

 **Also check out the prequel one-shot to this story "When You Wake" if you haven't yet, essentially it explains how Cas got Dean out of hell and some of the explanations behind why he is the way he is when he meets Dean topside.**

 **Anyway, enjoy, not really any torture scenes in this chapter just so you know.**

Chapter Four

"This is a locating spell that should at least tell us the general vicinity of where Dean is being kept," Castiel explained to Sam as he drew on the table in the motel room with chalk. "Do you have anything of his? Preferably hair, or something that he keeps on his person."

Sam searched the room until he finally was able to get some hair off of Dean's comb. They hadn't even gotten a chance to unpack before Castiel and Uriel had come to get him. He gave the hair to Cas and watched as the angel put it into a bowl with several other ingredients then started chanting in a language Sam couldn't identify. The bowl suddenly burst into flames and Castiel staggered slightly, bringing a hand to his head as if he had a headache. Sam reached out instinctively and gripped his elbow, steadying him.

"You good?" he asked. "Did you find them?"

"It's difficult—they are heavily warded. I can only get a vague location, but it seems they are somewhere nearby; not very far from where we had Alasdair previously." He opened his eyes. "If we can get in the vicinity then I should be able to sense where they are just from the warding alone."

"Let's go then," Sam said, grabbing the Impala's keys. "How did you do that spell by the way?"

"It's typically used for locating angels who have been lost or gone off the radar. It was not ideal, but I have a sort of bond, if you will, with Dean that allows me to have a somewhat stronger connection to him."

Sam frowned as he got into the car. "The…handprint on his shoulder?"

Castiel nodded. "To get him out of hell, I had to lay claim to his soul. It leaves a mark, though Dean probably doesn't feel the psychological connection like I do. Humans typically don't have the heightened senses to do so."

Sam felt slightly insulted, but shook it off, knowing the angel didn't necessarily mean it as offensive, just matter of fact. "So when we find where Alastair is keeping Dean, what do we do? If it's warded, you can't really go in, can you?"

"No, you will have to go in and destroy the warding first."

"Okay, and I guess in that time we hope that Alastair doesn't figure out that someone shut down his security system."

"If it comes to that, we will do what we must," Castiel told him. "But I will warn you, Sam. Alastair is a high-ranking demon, quite like Azazel. He's working directly for Lilith, and he is stronger than any demon you will have gone up against. If it comes to the point where you are forced to go up against him alone, do not assume you can win by caution and calculation. Strike first if you have the chance because he will not hesitate to kill you or worse."

"Okay, I'll remember that," Sam said. They drove for a while, Sam tense and worried about his brother and the possibilities of how badly this rescue could go, before Castiel started speaking again.

"I wish to apologize for last night's conversation," the angel told him.

Sam shook his head. "You didn't want to disobey orders, I get it. It's probably not much fun being on heaven's naughty list."

"No, it's not," Castiel replied flatly and Sam frowned as he turned to look at the figure sitting beside him. He was about to inquire, but Cas didn't give him the chance. "The truth is, Sam, I know there is a traitor among our ranks. I found the last angel who was murdered, and she had been stabbed with an angel blade. I had…concerns about such things previously, but heaven seemed to be keeping it under wraps and now I know why. It is hard to think that one of our own would be doing this, but nor do I believe it inconceivable. It saddens me, but I know it is possible, Sam, and I should not have tried to defend them to you."

"Look, Cas," Sam said, sighing. "I know how hard it is to believe that people you trust could betray you like that. And I'm sorry too, for being so uncaring about it. I know they're your family, and it must be hard to pick sides."

"I have to do my duty," Castiel said. "Suss out the perpetrator and see that justice is served."

"You really don't think it could be Anna?"

"No," Castiel said with certainty. "She may have every right to have a grudge against heaven, but I know her. She would never want this, and she warned me at great cost to herself which is why I am even more inclined to believe her."

"Well, I'm sure you'll figure this out, but we need to find Dean first."

Castiel nodded once. "Agreed."

Sam looked ahead and drove in silence, wishing their lives were full of simple hunts again and even more just wishing he had his brother back.

* * *

 _Dean jerked awake with a_ gasp, cold water drenching him. He clenched his teeth, shivering and groaning as feeling came back to his body in full force, everything hurting.

A hand slapped his face and he looked up blearily to see Alastair leaning over him. "You with me, Deano? You didn't take that last bout very well, I'm disappointed. And here I was still going easy on you."

Dean didn't have enough energy to retort. His throat was raw from shouting and he could smell the sharp metallic tang of his own blood as the water dripped off his body onto the metal table, tinged pink. Alastair twisted his fingers into Dean's short hair and pulled his head back, coaxing him to open his eyes again.

"Had enough, Dean? How about we take a little break? I'll even let you up; stretch your legs, have a bathroom break even. It is annoying having you flesh and blood, all these little human needs."

Dean grunted, but watched with interest as Alastair undid his manacles, starting with his feet and then going to his hands. Dean wished he had the energy to attack the demon right there, but truthfully he knew he didn't. It would just be a sadly pathetic attempt. Maybe in a minute when his shoulders didn't ache so much from the awkward position his arms had been in for the past few hours—or how ever long it had been. He tried to roll over and sit up but even that proved too much. Alastair tsked, a cruel, mocking smile playing over his lips as he slipped his arm under Dean's back and eased him up.

"Poor little Dean, was the mean demon too hard on you?"

Dean growled out a half-hearted insult, but spent all his concentration on making his body work. Alastair pulled him to his feet and Dean winced as the wounds on his soles reopened and bled afresh when his feet met the cold floor. He staggered, humiliating himself by having to latch onto Alastair just to keep from falling onto his face.

The demon cooed at him like he was an infant. "It's okay, Dean no one's here but you and me. You don't have to be strong for me. You know I've seen you at your very worst."

Dean bit his cheek to bleeding to keep the tears of shame and anger at bay as he was forced to cling to the demon as Alastair led him over to a corner of the room before lowering him to sit against the wall, pointing to a bucket. "That's to do your business in if you need. I'll get you something to drink to give you a little strength for the next round." He straightened up then, an annoyed look on his face. "I'll be right back, it seems I have a visitor. Don't go anywhere." And then he left the room, the door shrieking shut behind him followed by a solid clunk, leaving Dean suddenly alone.

* * *

 _Alastair stepped out of the_ old factory building he had taken Dean to and met the angel with an annoyed expression on his face.

"You showed up just as we were getting to the good stuff," the demon said with a sneer. "If you want me to do the job, you need to give me some space."

Uriel stared the demon down. "Is it not enough that I am letting you get away free, hellspawn? I would do it myself but I don't have time to get my hands dirty."

"No, I would expect not," Alastair said with a grin. "Too busy killing angels, if I miss my guess."

Uriel smiled grimly. "I do what I must. But do not misunderstand me. I think you are an abomination, it is only my interest in freeing my brother that leads me to work with you."

"And Lucifer will be freed, don't you worry," Alastair told him. "Especially when I kill the man who's supposed to stop him."

"Hurry up then, you have his brother and one of my garrison on your trail and getting closer."

Alastair laughed. "Sam Winchester, the boy with the demon blood, and Castiel, correct? The little angel on Dean's shoulder, the one who took away my best student. Don't worry about them, if they come sniffing, they'll get more than they bargained for."

Uriel didn't seem too amused. "Still, I don't have time for your games. Now I had best go before I am missed." He disappeared and Alastair sneered at the place he had been standing before going back inside, chuckling to himself.

* * *

 _As soon as Alastair left, a_ sudden fear gripped Dean as he wondered if the 'visitor' might be Sam, but Alastair had looked annoyed and not conniving as he probably would if he thought he would soon have Dean's brother in his grasp. No, maybe it was the angels come to find him after all. Dean hoped so, even if that sounded weak. He was just in so much pain and was tired of fighting it. He just wanted to be back at Bobby's in a clean bed, safe, and knowing that Sam was as well.

He looked down at himself, at the burns and the new work Alastair had done with the razor. His chest and stomach were covered in slices and stab wounds, but nothing too damaging. It just hurt and he'd lost a good bit of blood. Alastair had always been very talented at using that small blade in just the right way to cause maximum pain but minimum damage so the victim could last longer.

He groaned as he fought to get to his feet and decided to take a leak as Alastair had suggested while he had a moment alone. When he was done with that he looked back over to the table and the cart of instruments and slowly made his way back over there, hoping to find something he could defend himself with. Because when Alastair came back, he wasn't going to let him put him on that table again. In fact, he might just escape now.

He stumbled over to the table and was surprised when he saw the demon knife sitting there among the other torture implements. Alastair must have taken it when he had knocked Dean out. He fought to catch his breath, already exhausted, before he made the long trip to the door, not bothering to hold in his whimpers and moans. His whole body friggin' hurt, he was entitled to a little bitching especially since no one was around to hear him.

He finally made it to the door only to find that when he tried to pull it open it was locked or barred or something on the outside.

"No, no, no, no," he groaned, slamming his shoulder into it before he decided that was more than his body could take at the moment and just leaned against the door, panting. Okay, plan B; he would wait for Alastair to come back and then…

The door opened inward and Dean sprawled onto the floor, unable to keep his feet. Alastair stopped and looked down at him with something akin to disappointment.

"Well, it's good to see you're feeling a little better, Dean. But I'm afraid you're not going anywhere. You don't leave once you've checked in here." He reached down and grabbed Dean by the back of his ripped shirt, hauling him up. Dean grunted, but wasted no time in exerting all his strength into bringing up the knife. He had meant to jam the blade straight into the demon's heart, but Alastair shifted and he missed and only caught his upper arm instead.

The demon looked down at it with a snarl but rolled his eyes. "Come on, Dean. Are you serious? You really thought this was going to work? I must have really scrambled your noggin'." He pulled it out and tossed it aside with a clatter. Dean groaned as Alastair hauled him further upright. "It appeared my lessons still haven't stuck. That's going to cost you." He slammed Dean into the wall face first and the hunter yelped and slumped to the floor, his head spinning.

When his vision cleared he saw Alastair crouching over him and he couldn't hold back a whimper as he knew he had failed and no one was coming for him and he was going to have to endure hours more of torture. Alastair clicked his tongue at him reprimandingly.

"Dean, Dean, Dean, what am I going to do with you?" he hauled him to his feet and drug him back to the table. Dean tried to fight, but Alastair was too strong and he simply heaved him bodily onto the table by the back of his jeans and chained him up again. He tightened the strap around his right wrist before taking Dean's chin roughly and forcing him to meet his eyes. "You can't expect me to go light on you anymore. We're going to have to work to get my lessons into your skull." He tapped the center of Dean's forehead before he turned and dug his fingers into one of the wounds in Dean's stomach. Dean screamed in shock and agony, writhing and arching his back.

"What's the matter, Dean? Can't take the pain? Don't you remember how you made those poor souls scream in hell? You did worse than this and you just ignored them when they pleaded with you to stop. Don't you think this is fair turnabout? Hm?"

Dean fought back a sob and choked out another scream as Alastair turned his attention to another wound, digging deeper into him, as the mental agony mixed with the physical. Because deep down, he knew he did deserve this. For everything he'd done, for everything he'd _felt_ when he had tortured those souls. Knowing he had done it wouldn't have been so bad if he hadn't enjoyed it so much. Because he had and he wasn't going to deny it, he couldn't deny that. He deserved to feel their agony now, again, and if he were to die like this, then so be it. Maybe this was why the angels had brought him back. Not to give him a second chance in life, but to give him a second chance in hell.

To see if he would break again.

And that was when Dean started sobbing, because he knew it wasn't going to change a thing.

* * *

 _The day Dean finally broke was something he would never forget._

 _Thirty years, it had been. For thirty years Alastair had spent each day carving Dean up and torturing him in ways he had never imagined a person could be tortured, both physically and, even worse, mentally. The pain itself wasn't anything compared to the twisted perversions he was forced to endure, especially the hallucinations that involved his father and mother, and Sammy. It all became too much, but the point of fact was that Dean was tired. He was too tired to fight anymore, and Alastair sensed this. He came to him that last day, when Dean was at his worst, a lower point than he had ever been brought to before and in that moment, he would have said anything to make it stop. All the anger, the frustrations, the self-hatred, and pain and pity were at their heights and he just couldn't fight anymore. All his walls had fallen and he felt like there was nothing left._

 _"What do you say, Dean?" Alastair asked him almost gently, his hand, stained with Dean's blood, combing through his hair in a mockingly soothing gesture. "You promise to pick up the blade for me, I'll take you off this rack and you don't ever have to go back on it again."_

 _Dean sobbed, turning his face away from the demon, ashamed at his wanting to give in. Knowing what his father would say, knowing how much it would hurt Sammy to know he had given up. But he couldn't even find it in himself to be sorry. He just didn't care, didn't have the capacity anymore. He was broken, utterly destroyed, and he found himself speaking before he knew what was coming out of his mouth._

 _"Alright," he whispered and felt the hand stop stroking his hair._

 _"What was that, Deano?" Alastair brought his ear to the broken man's lips._

 _"I said alright," Dean ground out. "I-I'm done."_

 _"That's excellent," Alastair told him and Dean felt the chains giving way before he opened his eyes again. He fell to the ground but strong hands lifted him up and he felt his body whole again suddenly. But it didn't matter. Inside, was where all the real pain was. The dark hole that was his soul now, shattered and so far beyond repair it was almost unrecognizable._

 _"Come on then, my boy," Alastair told him, gripping his shoulder and pulling him away. "Let's put you to the test then, shall we?"_

 _He was led to another cell and there was a woman strapped to the table. Dean blanched, but Alastair pushed him forward firmly._

 _"No time for your chivalry," he told the Winchester. "You see, she's not a very good person, if you only knew what she'd done to her children you wouldn't hesitate. Take my word for it, Dean, she deserves anything you will give her."_

 _"No, no please!" the woman screamed as Alastair led Dean to the table and nodded to the tray of instruments at his side._

 _"Pick it up, Dean. If you can't do it, I'm just going to have to put you back on the rack yourself."_

 _Dean's hand shook as he reached down and took up a razor like the one Alastair favored. He stared at it, taking deep breaths before he turned to the woman, still screaming at him not to._

 _"It's easy, Dean," Alastair told him, taking his wrist and pushing his hand toward the woman. "It slices as easy as butter."_

 _The blade touched skin and there was a long scream and Dean's eyes closed as he took a shaky breath. The sharp smell of blood filled his nose, so much more prominent in that moment even though he thought he would have been used to that smell by now._

 _"Good boy," Alastair told him with uncontrolled glee, petting his head affectionately as if he were a favored dog. Dean supposed that's what he was, really. "Do it again."_

 _He did._

 _Dean didn't know it was possible for someone to break twice, but it must have been, because he did that day, cutting into that woman. Because it wasn't the fact that he had given in. It was the fact that in some twisted way, he liked the turnabout._

 _It felt good._

* * *

" _We've been driving for hours, Cas_ , are you getting anything?" Sam asked tiredly as he turned down another street, his eyes swimming in the late afternoon light and his head aching, his stomach a tight knot that seemed to have given up on the thought of feeling hungry.

Castiel looked tired too, shaking his head. "I haven't sensed anything yet. Perhaps we should stop for a while, get our bearings."

"I'm not stopping until Dean is safe," Sam snapped.

"Sam it's been at least thirty-six hours since you slept," Castiel told him firmly. "Or eaten much of anything. You need to rest or you're not going to be any use to your brother, or in a fight against Alastair. In this state you could only compromise our mission at best if not end up dead."

Sam scowled. "I'm fine, Castiel."

"Sam," Castiel said in a firm, no-nonsense voice. "Is this what Dean would want you to do? Run yourself into the ground? You should find a motel and get a few hours of sleep. I can look around while you do, it will be easier for me to travel by myself and I will be able to see more when I'm not in this vehicle."

Sam set his jaw, wanting to protest, but he knew Castiel was right. He was exhausted and close to falling asleep at the wheel, which wouldn't help anything. And yeah, if he could hardly drive, he knew he was in no fit state to go against one of hell's most high-ranking demons, especially if he might have to face him down alone. It wasn't ideal, but it was better than being killed before he could rescue Dean, he supposed.

"Fine," he said tiredly. "I guess you're right." He pulled off at the next motel they found and Castiel turned to him before Sam went to book a room.

"I'll let you know if I find anything. If not we will continue our search later tonight." And then he was gone. Sam was getting annoyed with that.

He checked in and dragged his bags into the room. He decided a shower was probably a good idea but after that, he was so exhausted that even thoughts of Dean's predicament couldn't keep him up and he fell asleep on the covers, dead to the world.


	5. Chapter 5

**Back again! Thanks again to everyone who was reviewed, followed and faved, I always love hearing what you guys think :) Sam and Cas are finally getting closer to figuring out where Dean is.**

 **Some of the dialogue in this chapter was taken directly from "On the Head of a Pin"**

 **Warning: more torture in this one, at the end, but mostly just Alastair messing with Dean's head.**

Chapter Five

Castiel searched everywhere in theimmediate vicinity and then further afield until he wondered if maybe his tracking spell hadn't been entirely accurate after all. Not only could he not sense Dean or Alastair anywhere, which had been expected, he couldn't sense any warding either—which had not been. Even earlier he had felt that odd void that was still _something_ that he always felt when there was warding, but now he couldn't even feel that. He wondered if Alastair had moved to a different location. But that didn't make sense; moving Dean would have put him outside the warding even if it was only for a second. Castiel would have been able to feel it and he had felt no such thing happen. Something else was going on here and he had the feeling it had something to do with the other problem.

Because, the more he thought about it, the more he realized that if there was an angel killing other angels, for whatever reason, maybe they had been working with Alastair to begin with. But why? And why risk Dean? He was the only one who could stop the apocalypse, at least as far as Castiel knew, and why would any of the angels wish to ruin their chances of winning the war? It was very troubling to think that any of his comrades would wish the outcome to be so dark, but with everything else that had been going on, he couldn't rule it out either.

He searched some more, but by the time dawn came around, he still was no closer to finding Dean and he was feeling very discouraged. Perhaps the warding kept even his angelic senses from picking up anything. Maybe Sam would have an easier time of it.

He appeared in Sam's motel room with a hot breakfast a little later. Sam sat up with a start when the angel called his name and looked in exhausted confusion from Castiel to the hot food sitting on the motel table. Castiel motioned to it a bit self-consciously.

"I…thought I would bring you something to eat so you could get started. Bacon and eggs, and coffee."

Sam rubbed the sleep from his eyes. "Thanks, Cas," he said, surprised and slightly amused. The smell of the coffee and bacon made his stomach growl sickly and he realized he was starving. He got up and attacked the food, before he spoke with a full mouth. "Did you find anything last night?"

Castiel shook his head. "No, I'm sorry, Sam. There is something…else. The warding is very good. Too good; at least for a demon."

"What are you saying?" Sam demanded, gulping coffee.

Castiel inhaled slowly, weighing his words. "I…fear that the warding is Enochian in construction. It seems that I was correct in thinking that an angel was involved in the treachery, likely with Alastair. Only an angel would know how to ward so completely against other angels without us being able to even detect the warding itself."

"So how are we going to find Dean?" Sam demanded, getting frustrated.

"You aren't."

Both the hunter and Castiel turned, Sam jumping to his feet, as Uriel appeared in the room. Sam snarled at the angel.

"What do you want now? What do mean we aren't going to find Dean?"

"Castiel, what are you still doing with this…abomination?" Uriel asked, looking Sam up and down like he was something scraped off his shoe. "I thought you were reassigned."

Castiel came forward to stand slightly in front of Sam as if he were afraid the young man would try something. The motion surprised Sam slightly, reminding him of Dean. "I convinced them to keep me on this mission until Dean was recovered."

"Well, no longer," Uriel said with a hint of pleasure in his deep voice. "Dean Winchester is no longer a priority."

"What are you saying?" Sam demanded. "What happened to Dean?"

"Nothing's happened to him," Uriel said. "At least as far as we know. It is simply not our problem anymore. You, of course, may search to your heart's content, but Castiel must return to his own duties."

"What are you saying, Uriel?" Castiel asked, stepping toward the other angel. "How is recovering Dean Winchester no longer our priority? We need him to see this through."

"Perhaps not as much as you think," Uriel said. "But that matters not. In case you forget, Castiel, our comrades are dying, murdered. That is our priority, to make sure no others fall."

"But, I believe that the murders have something to do with Dean's disappearance," Castiel insisted. "Uriel, you must suspect as I said before that an angel is responsible for this. I believe they also released Alastair. We must capture him again; try to get the information out of him. He might have even told Dean who the traitor is, thinking that he wouldn't return to us alive."

"Enough, Castiel," Uriel said firmly. "I am your superior now, in case you forget. If you are not where you should be by the end of the day, I will drag you back to heaven myself and I don't think you want that, do you?"

Castiel seemed to shrink before Sam's eyes. He didn't get a chance to reply before Uriel was gone.

"Cas, what is this about?" Sam demanded as Castiel turned, looking somewhat lost. "Why have they dropped Dean?"

Castiel sighed. "I don't know, but something is wrong. Very wrong. I don't know that we can trust any of the orders."

"What do you mean?" Sam asked.

Castiel turned to look at him. "Anna said that it was possible the orders we are receiving are no longer coming directly from God, but perhaps another angel vying for authority in heaven. I suspected it for a while now, but even more when we were told Dean should be brought to torture Alastair."

Sam listened thoughtfully. "So, you think this could be from the angel who is killing the others?"

"It's possible."

"But tell me this, because I don't understand," Sam demanded. "You saved Dean, you went to hell for him, but why? He broke in hell, and, look, don't get me wrong, I love my brother and he is a good man, but righteous? Cas, I want you to be straight with me, because I can't be in the dark anymore, especially not now when Dean might have been kidnapped under the orders of the people we thought were on our side. You owe me that much."

"Yes, you're right." Castiel was silent for a long moment before he sat down at the table opposite Sam. "There's something you need to know about your brother, Sam. I called him the righteous man because he is. He was not meant to go to hell, he went there for you and that is a noble thing indeed. The same as your father who went for Dean. In fact, it was supposed to be your father."

"What was?" Sam demanded before he stopped himself as Castiel looked at him with annoyance for being interrupted. "Sorry."

"There is a prophecy that states that the first seal would be broken when a righteous man sheds blood in hell. But your father never broke, and then he got out when you opened the devil's gate. But then there was Dean, and he broke in hell, Alastair made sure of it." Castiel looked pained, showing more emotion than Sam had seen. "And so the first seal was broken."

"So wait," Sam said, trying to understand what he had been told. "The…first seal? You mean…Dean… _started_ all this? The _apocalypse?_ " His voice was barely a whisper at the end, unable to fathom the enormity of it all. His brother—responsible for the end of the world? How the hell was Dean ever going to survive knowing that?

Castiel nodded grimly. "Yes."

"Then…why?" Sam asked, unable to say anything else. "Why did you save him?"

"Because the prophecy also states that the man who starts it is the only one who can end it. I was too late saving Dean from himself, but I did save him to give him a second chance to help stop this."

"But he didn't know, he couldn't have," Sam cried, feeling tears threaten behind his eyes, horrified at this knowledge and even more at the thought of Dean finding out about it, as he was bound to eventually.

"No, he didn't," Castiel said gently. "It was not supposed to be him. He didn't know what he did by stepping off the rack."

Sam shook his head angrily. "As usual, Dad put all his problems on Dean's shoulders even when he didn't know it. I swear…"

"Do not put this on your father, Sam, he didn't know either. It was going to happen either way. It is my fault it wasn't stopped to begin with."

Sam shook his head again and walked quickly to the bathroom, shutting the door behind him. Castiel stood awkwardly for a moment, before he realized the hunter probably wished to be alone.

"Sam, I'll…be back soon."

He left the motel room and walked out into the deserted parking lot. It was still early, only milky dawn and he took a deep breath of the fresh air. The utter horror and sadness Sam had shown for Dean's sake had shaken him in a very emotional, very _human_ way that he couldn't explain. He had become too close to the Winchesters, but at the moment he didn't really care either. He was confused enough with everything else, he didn't have time to think about this too.

On impulse, he called to the one person who might be able to help him just then, hoping that a familiar face might give him the strength to do what he knew he had to do.

"Anna," Castiel called, hoping she would answer, though it was unlikely, he thought sadly. "Anna, please."

To his surprise he became aware of another angel behind him and he turned to see his old superior standing there.

"Decided to kill me after all?" she asked bitterly.

"I'm alone," he told her.

"What do you want with me, Castiel?"

He hesitated, looking down, unable to meet her eyes. "I'm…considering disobedience."

She seemed surprised to hear this and nodded slightly. "Good."

"No," Castiel said firmly. "It isn't. For the first time…I…feel…" He didn't know what else to say, or rather didn't want to voice it out loud. The foreign emotions he had been experiencing of late, doubt at the forefront, had not been in the least pleasant.

"It gets worse. Choosing your own course of action, it's…confusing," Anna told him gently, coming closer now that she was sure he wasn't going to kill her. "It's terrifying." She touched his arm and he looked down, shifting away from her in shame. She sighed bitterly. "That's right, you're too good for my help. I'm just trash, a walking blasphemy." She turned and started away but Castiel stopped her.

"Anna," he called. "I don't know what to do. Please…tell me what to do."

"Like the old days?" she asked with a wry amusement. "No, it's time to think for yourself." And then she was gone, leaving Castiel alone once again with only his rebellious thoughts to keep him company.

It should not have to be like this. How had they come to this? Angels going behind each other's backs and creating chaos; working with demons, and having their brothers and sisters murdered. He didn't know what to think anymore, he was so confused.

But there was one thing he could do and that was help Sam Winchester find his brother. For whatever reason, Sam and Dean gave him hope. Dean might have been broken in hell and Sam might have demon blood in his veins, but they were capable of more than even they realized, and Castiel felt sure, if he was sure of nothing else at that moment, that they would be able to stop the apocalypse even if all else failed. He had to have that faith at least, because it didn't look like there was much faith to be had in anything else just then.

He came back to the motel room just as Sam was coming out of the bathroom, seeming more together than he had when Castiel left. "Let's go find your brother, Sam. I think I have an idea of how to do it."

The younger Winchester seemed surprised by this. "But, Cas, Uriel said…"

"I know what Uriel said," Castiel said shortly, not wanting to think of the other angel at the moment. "But I am going to follow my first and foremost orders and that is to look after my charge."

"Are you sure?" Sam asked, shifting awkwardly. "I don't want you to get in trouble either, Uriel said he'd drag you back to heaven by tonight if you didn't go quietly."

Castiel looked at him with determination. "Then I guess we'll just have to find Dean before then."

* * *

 _The pain was all encompassing_ , flaying every nerve in his body both psychical and otherwise. Dean barely had the power to think straight anymore. This was different than it had been in hell, more grounded, more vital, and in correlation with those thoughts he knew that he was fading as his blood seeped away, down his sides and onto the table, some of it even dripping onto the floor now. He was a disaster, and Alastair just kept carving and burning and never stopped for even a minute, all the while chuckling to himself or making comments Dean didn't have the energy to think up comebacks for anymore.

Just then, the demon was humming some jaunty tune as he casually dug his blade into Dean's belly. The hunter choked out a strangled sob, his whole body tensing in pain, with no time to recover before there was another cut and another.

"S-stop," he finally gasped out.

Mercifully, Alastair did, sliding his razor carefully from Dean's flesh, causing his breath to hitch before his body fell limp on the table, only his chest heaving from agony and exhaustion.

"Stop?" Alastair asked mockingly. "Don't tell me you've had enough, Dean, we've only been at it, hmm, about two days now. I know you're mortal up here on earth, but I expected a little more from you at least. Though you _are_ damaged goods, I suppose." The razor almost caressed his cheek, scraping against the stubble there in a grating sound, making Dean shudder as Alastair traced it down his throat and over his shoulder to rest across the handprint shaped burn Castiel had left on him. Alastair pressed the blade to it, pretty much the only unmarred patch of skin he had left, but then lifted the blade and set it aside, taking Dean's jaw in his bloody hand and pulling his face upright.

"If you want me to stop, Dean, I'm sorry to say that's it. My orders were to kill you, after all, and I've apparently already taken more time than was proper." This was said mockingly with exaggerated eye rolls. "So are you ready to die, Dean? Hmm? What would poor little Sammy think finding your disemboweled corpse outside his motel room? Or maybe I'll just leave it in that car of yours. I would imagine your angel would be a bit upset too. I hear that he's defying orders looking for you." Alastair chuckled putting his hand over the burn scar briefly before snatching it away as if touching something disgusting. "I'll admit, I wouldn't have expected anything of the sort from an angel, had I not seen what he went through to get you out of the pit. It seems the poor pigeon thinks he's your guardian or something. It's sweet, you have to admit—in a vomit inducing sort of way."

Dean watched Alastair through slits of his heavy eyelids, exhausted, trying with everything he had not to pass out. He hadn't slept or eaten for the whole time he had been there and the only water he had drunk had been the blood-tinged stuff that dribbled into his mouth every time Alastair had thought he needed a refresher. And he was cold, so cold he shivered, especially now, thinking of his imminent demise. Alastair noticed and let go of his chin, bringing the hand up to instead caress his cheek, rubbing his thumb across the bruised and bloody skin to wipe away the tears that were falling unbidden from Dean's eyes. The hunter tried to jerk away but Alastair leaned over, his face too close for comfort, and starting stroking Dean's hair with his other hand.

"There, there; poor boy, I've really put you through a lot, haven't I? I wish I didn't have to, Dean. You brought this upon yourself. However, counteroffer," he leered into Dean's face, the hunter flinching instinctively. "You come back and work for me and we can call it even."

"N-never," Dean forced out.

Alastair tsked. "Aw, Dean, after all the good times we had together? I didn't even get to teach you the best stuff. There's oh so much more fun to be had. What do you say? Be my apprentice again? In a few centuries you'll be my best student, ready to teach others, I'm sure. Never did I see such promise."

"Shut up," Dean groaned, jerking at his chains and ducking his head away from Alastair's falsely gentle hands. "L-leave… me alone. If—if you're gonna kill me, do it…you bastard."

Alastair straightened up slowly with a deep sigh, shaking his head. "Should have known you weren't quite there yet. I suppose that just means another session is in order." Dean couldn't bite back the whimper that escaped as he saw Alastair reach for the brand again. "Looks like I'm going to have to step up my game again, hm, Dean?"

Dean closed his eyes, as if that would make it any better, but the burning didn't come this time. He heard Alastair curse and slam the brand back onto the cart. Dean looked over curiously.

"Seems we'll have to postpone," Alastair said with a small smirk. Dean's stomach clenched, not liking that look at all. "Looks like we're going to have some visitors soon, Deano."

 _Sammy._ Panic filled Dean and he jerked at his chains with the little strength he had left. "Alastair, I'm not gonna let you hurt him, I swear, if you touch him, what I did to you before will only be the beginning."

"That's adorable, Dean," Alastair told him patronizingly. "Tell me that again when I have him screaming." He grabbed a rag from the cart and forced it between Dean's teeth, tying it behind his head to muffle any warnings he might have. "Be right back, my boy," the demon grinned and picked up a long blade, heading toward the door.

Dean grunted past his gag, and yanked at his chains, but he was too weak and that small exertion took its toll on him, causing everything to go fuzzy around the edges, until he was only vaguely aware of the sounds of a fight going on outside the room he was in, and he didn't have enough strength to care.


	6. Chapter 6

**Okay, guys, finally the promised rescue, but that's not the end of the story quite yet either ;) Thanks again to everyone who has reviewed, followed and faved, keep letting me know what you think!**

 **Also, if you haven't yet read the prequel one-shot to this story "When You Wake" check it out, because there's some stuff mentioned in this chapter that took place in that story that's based off a couple head canons of mine. So if you're confused at all during this chapter, that's why, and don't worry, you didn't miss anything ;) And also, I kind of tried to give explanations for things that happened in this episode that the show never explained. Maybe they'l hire me? :P**

Chapter Six

"Stop here, Sam."

Sam did what Castiel told him and pulled off to the side of the road, parking the Impala and cutting the engine. "What now? Do you sense something?"

"Not quite," Castiel admitted. "It's more of what I don't sense. It's very hard to explain but the concealment sigil that was used is likely blocking everything, acting more as a diversion than an actual concealment. As if it's telling me to look in the opposite direction."

"So what is your plan?" Sam asked him, trying to be patient, knowing the angel was helping him at great risk to himself, but also knowing that any minute they spent looking would be another minute Dean would be under Alastair's control, and they had already wasted too much time as it was.

"Look where my mind is telling me not to," Castiel told him simply. "I have passed over this section of town several times in my searching, giving it no real notice, and I think that's what we're looking for. Once we encounter the right place, I'll be able to tell you for sure."

"So we just walk around until we find it?"

"We have no other option."

Sam nodded and got out of the car, opening the trunk and grabbing several items in a duffle bag. He wished he had the demon killing knife, but it hadn't been in the room when he and Cas had gotten there and he could only assume Alastair had brought it with him. But at least Cas' angel blade could take out a demon. He closed up the trunk with a deep breath, and turned to Cas. "Let's go."

They walked down the street and Sam realized it was an ideal part of the town to hide Dean. There were a lot of old, dilapidated buildings and factories to hide prisoners and no one around to hear…well, Sam knew he wasn't going to find Dean in a five-star hotel. He was probably going to be in pretty bad shape unless by some miracle Alastair hadn't gotten around to torturing him yet. He cast a glance over at Castiel who had his brow furrowed, concentrating fully on the task.

It seemed ages before the angel stopped and turned to the hunter. "There, I think that's it." He pointed to an abandoned factory building standing at the end of the street they were on. He and Sam hurried forward and Castiel touched the building, pulling his hand away quickly. "Yes, this is it."

"I don't see anything," Sam frowned, looking for painted sigils.

"They're inside," Castiel said. "You'll have to go in and disarm them. The concealment ones aren't going to keep me out, but the Enochian sigils will be at each corner of the building. They'll look like this." He bent and swiftly sketched a sigil in the dirt at their feet. "Go fast, you need to get to them before Alastair finds you, he'll likely know once you start disarming them."

Sam nodded, swallowing hard. He reached into his bag and took out a can of spray paint. "Okay. See you soon." He started inside when Castiel stopped him.

"Sam, wait," the Winchester turned around and saw the angel hesitatingly holding out his blade. "Take this just in case. You can give it back to me once I get inside."

Sam slowly closed his hand over the hilt of the weapon, feeling the perfect balance and examining the deadly three-edged blade. He knew Castiel must trust him to give him this weapon. The gesture touched him, made him feel less like the abomination with the demon blood, and he smiled at the angel with a nod. "Thanks."

"Go, Sam," Castiel told him.

Sam turned and went inside. It was dark, and he pulled out a flashlight, hurrying to the east corner first which was closest. Thankfully he found the sigil there, and he quickly X-ed over it with the paint. Knowing he didn't have much time now, he raced to the next corner and disarmed that one too. Then to the last two.

He was on the last one when he heard a step behind him and spun around, seeing Alastair standing there, a long knife in his hand that he was caressing with the opposite thumb.

"Well, well, if it isn't little Sammy Winchester, come to rescue his brother, no doubt. How sweet."

Sam swallowed hard, the demon's chilling nasal lisp freezing him in place, as well as the sight of the blood soaking his shirt and hands. Alastair caught his gaze and chuckled as he advanced.

"If you're wondering, yes, it's all Dean's. He's gotten a bit rusty since he left hell, I was simply giving him a refresher course."

"You bastard," Sam snarled, raising the paint in the hopes of destroying the sigil before Alastair got to him.

The demon simply flicked his wrist and the can went spinning from Sam's hand. The hunter backed against the wall, drawing out the angel blade from inside his coat.

"My, my, what a fancy thing for a hunter to be carrying," Alastair said mockingly. "Was the pigeon too afraid to come?"

Sam gritted his teeth and instead of using the blade on Alastair, which he saw would be futile, he turned and slammed it into the sigil, hoping that would be enough to break it. Alastair was right in front of him then, and gripped his throat, heaving him up until Sam's feet left the floor, choking for breath. He felt the sharp tip of Alastair's blade pressing into his stomach, threatening to gut him if he made a sudden move.

"We're going to go see big brother now, I'm sure he'll be glad to see you."

"Let him go, Alasdair."

Sam saw Alastair smile, then he was released to crumple to the ground gasping. He saw Castiel standing behind the demon, and was glad the blade in the sigil had worked after all except that now the angel was unarmed.

"Castiel," Alastair said mockingly. "It's been a while. Have you come to take Dean from me again? You have to admit that's cruel, seeing as I caught him this time fair and square, just like you did last time."

Sam struggled to his feet, reaching for the blade, but his fingers only grazed it before Alastair flung him off his feet and into the wall. Sam hit hard face first and fell to the ground, his vision blackening and blood dripping from his nose and mouth. He was surprised he hadn't bitten through his lip.

"Let the grownups talk, boy," Alastair sneered at him.

"I don't have time to play games with you, Alastair," Castiel told the demon firmly. "Come quietly and I won't have to kill you."

Alastair laughed. "You really think I'm going to let you take me alive? Even if you did, who would you get to torture me, hm? Your…head interrogator is a little, hm, tied up right now!"

Castiel stepped forward. "Then just tell me who let you out, who hired you to kill the angels?"

Alastair chuckled again. "You really think I did it? No, I was only supposed to get rid of Dean, the demons aren't responsible for your garrison's recent death toll. Not that I wouldn't have, of course."

"Who, Alastair?"

Alastair just grinned and chuckled. "No, it would be so much crueler to let you find out from the source. I'm sure you will eventually, if I don't kill you now, that is."

He lunged and grabbed Castiel by the coat, but the angel brought up a hand and forced a palm against the demon's head. Alastair's eyes turned milky white, but he laughed.

"Bit above your pay grade, I think," he said and threw the angel to the ground, kicking him several times before hauling him back up and slamming him against the wall, the blade at his throat. "I should have killed you back in hell when I had the chance. I just thought Dean would pull through, do it for me. Should have known you would have gotten into his head. Not going to make that mistake again." He hit Castiel several times with the blade hilt before throwing him to the ground again. Castiel groaned and tried to roll to his feet, but Alastair kicked him back down, a foot pressing into his chest. "You really are pathetic, aren't you? Can't even get rid of one demon." He shook his head. "Now if only I could kill you, but I can only send you back to heaven."

Alastair started chanting as Sam finally managed to get to his feet, his head spinning, but determined, as he staggered over to where Castiel's blade was still stuck in the wall. He grabbed it and yanked it out, watching in horror as Castiel's body tensed, and his eyes started glowing bright blue as if he was being pulled out of his body.

"Hey!" he shouted, hoping to distract the demon, and slammed the angel blade into his back so hard the point exited through the front of his shoulder.

Alastair staggered, and stepped off of Castiel so the angel could haul himself to his feet slowly. The demon started laughing as he turned around to face Sam, the hunter stepping back as he realized he hadn't quite hit the mark.

"Good try," Alastair told him, reaching around and pulling the blade out with a grimace. "Maybe next time you won't miss." He threw Sam into a wall and kept him pinned there. Sam grunted and struggled but soon realized there was no hope of getting free, Alastair smiled. "Good boy, stay now." He turned back to Castiel who was panting, looking like it was an effort just to keep himself upright. The demon tsked, shaking the angel blade at Castiel as he advanced.

"Just you and me now, Cassie. And I'm not going to make the mistake this time of trying to get Dean to finish you; no, I'll take the pleasure myself. Maybe let him watch, while I take both you and Sammy-boy apart. I don't think he'd like that, do you?"

Castiel bared his teeth and lunged at Alastair, grabbing for his wrist to wrestle the blade from him, but Alastair grabbed him by the throat, slamming him against the wall. He used the blade to flick aside Castiel's trench coat and dug the tip into the flesh above his heart, leaning in close.

"I've always wanted to see what one of these could really do," he said gleefully as he carved a deep furrow to the middle of Castiel's chest, blood and grace seeping out as Cas grunted past clenched teeth. Alastair was pleased. "That's good hm, very good. You know how long I've thought of doing this to you, Castiel? For taking my best student away form me? I was fast becoming a mentor, a… father figure of sorts to the boy and then you had to come in and ruin that…connection. Steal him from me, leave your filthy mark on him." He spat into the angel's face. "And now you've come to take him again. But I won't let you this time." He cut across Castiel's stomach, eliciting another groan from the angel, before he sunk the blade slowly into his side and finally succeeded in getting Cas to scream.

"Cas!" Sam called frantically, renewing his efforts to escape Alastair's clutches.

"You'll get your turn soon enough, Sam," Alastair told him as he changed his grip on Castiel, grabbing a handful of his hair and yanking his head back to expose his throat. He pressed the tip of the blade up under his jaw and put more pressure there until a trickle of blood seeped down. Castiel gritted his teeth and struggled, his throat bobbing as he swallowed.

"Nervous?" Alastair asked him. "Do you want to know how long it took me to get Dean to scream? It was the burning that finally did it. He doesn't like that, you know. Reminds him of how his mother died."

"You son of a bitch," Sam ground out, tears pricking behind his eyes.

Alastair spared him a casual glance. "I wonder if it would be the same for you, Sammy."

Castiel took the moment Alastair's head was turned to bring a knee up into his ribs and then kick him in the chest, sending the demon staggering several feet away. Cas swung a fist at his face and pounded his jaw several times before Alastair caught his fist and wrenched it around, slashing down with the blade across Castiel's shoulder blades. The angel screamed and dropped to his knees, barely registering Sam's frightened inquiries and Alastair's laughing as he wrenched him around by the front of his coat.

"Got you where it hurts, didn't I?" he gloated. "What do you say, little birdy, should I clip your wings permanently?"

Panting heavily and with a growl of effort, Castiel launched himself at Alastair and grabbed his wrist, forcing the blade into his thigh before he wrenched his arm back and made him drop it. Alastair screamed and the pain made him release Sam. The younger Winchester fell to the ground with a grunt and instantly scrambled forward to snatch the angel blade, falling into a crouch, and barring his teeth at the demon.

Alastair laughed at him. "What a brave puppy you are, Sammy boy. You think you can kill me?"

"It's Sam," the younger Winchester snarled. "And yeah, I do. This is for Dean, you bastard."

Castiel grabbed Alastair from behind the instant Sam lunged forward and drove the blade through Alastair's throat. The demon gasped, stiffening in shock and pain before his eyes sizzled red for several seconds then burned out. His body fell limp and Castiel dropped it without care, crouching to yank his blade from the demon's throat.

Sam breathed heavily, wincing as he touched the side of his head, brushing aside the hair that was matted with blood.

"Thank you," Castiel told him, wiping his blade clean on the demon.

"Same here," Sam said and the angel smiled slightly and nodded. "Now we need to find Dean."

"I can sense him, he's down below," Castiel said, frowning deeply. "He is in great agony."

Sam's stomach twisted as he watched the angel stand up from beside Alastair's body and stagger.

"Woah, Cas, you okay?" Sam asked, instantly stepping forward to steady the angel. Castiel, hunched, groaning a minute before he straightened carefully, lines of pain clear in his face.

"I'll—I'll be fine soon," he gritted out. "The wound on my back…because he had my blade he was able to damage both my vessel and my true form—injure my wings."

Sam swallowed hard. "Is—is there anything I can do?"

Castiel shook his head as he steadied himself. "I'm afraid not. It will take time to heal, I won't be able to fly for a while."

Which meant no angel-lifting Dean to a hospital if he was in critical condition. Sam swallowed, trying not to feel annoyed; Cas deserved more than that. The thought of him taking on Alastair, to get to Dean, taking on Uriel and the angels too for that matter, gave Sam a new respect for the angel and it wasn't his fault he had taken damaging wounds in the course of getting Dean away from the demon.

"Come, Sam," Castiel told him, motioning him on, "We need to find Dean."

Sam nodded sharply and hurried down some stairs, letting Castiel take the lead because he seemed to know where they were going.

"Here," the angel said, stopping at a barred door at the end of a corridor. He lifted the bar and opened it, entering the room, Sam close on his heels. The smell of blood and worse hit them and Sam pressed his hand to his mouth, fighting back the urge to gag. Then he looked over and saw Dean.

"Dean!" he cried, pushing past Castiel and running over to the metal table his brother was chained to. "Oh God, Dean." The younger Winchester felt his throat tighten as an unbidden sob escaped. Dean seemed to be unconscious, his body a mess of cuts and burns, blood soaking his ruined t-shirt and torn jeans and pooling under him. Sam gently touched his brother's face, turning it toward him and Dean jerked, his eyes flying open in panic, moaning past the gag in his mouth.

"Dean, Dean, it's me," Sam pleaded, fighting back his tears so he wouldn't distress his brother more. He forced a smile on his face and fought to undo the gag though Dean closed his eyes and groaned even more after seeing him.

"S-Sammy," Dean whispered, as soon as the gag was gone. "Y-you shouldn't have come. P-please… go."

"No, Dean, it's okay," Sam told him gently, working to undo the manacles. "Alastair's dead, he's not going to hurt you anymore, I promise."

"Dead?" Dean whispered, his eyes opening in slits of dulled green.

"Yeah, Dean," Sam insisted, the smile still fixed on his face. "You're safe now. We'll get you out of here. Crap, you're shivering." He shrugged his coat off after he had gently lowered Dean's arms down to his sides, and spread the coat over him, wincing as Dean cried out when the fabric touched his destroyed torso. He cupped his hand under the back of his brother's neck, trying to offer comfort without hurting him further. "Damn, I'm sorry, Dean, I'm so sorry."

Dean looked up at him. "No' y'r fault," he slurred, then flicked his eyes to the other side, as Castiel stepped hesitantly over to him. "Cas, you bastard," Dean croaked painfully. "I told you not to make me do it."

Castiel's face looked more remorseful than Sam had ever seen it. "I'm so sorry, Dean," he said quietly.

"Can—can you heal him?" Sam asked hesitantly, not wanting to ask more of the angel now when he had already done so much.

Castiel hesitated. "I may be able to take some of his pain, but with these injuries I don't have enough power to heal him fully right now."

"Just…do what you can?" Sam pleaded.

Castiel's eyes softened and turned to Dean, putting two fingers to his head for a second. Dean tensed then relaxed, is face un-creasing a bit. Castiel slumped and leaned against the table for a second while he watched Sam check his brother over again.

"We need to get him to a hospital," Sam said. "He's cold and in shock and he's lost too much blood."

"Let me," Castiel said and bent to slip his arms under Dean's knees and shoulders, lifting him like he was a child. Dean yelled in pain, but was too hurt to protest as he settled limply against the angel's chest. Sam set his jaw, his heart aching at the sight of his brother so broken. He was about to follow Castiel when he saw the demon knife on the tray with the torture implements. He grabbed it and put it in his belt, then saw Dean's amulet there too. He snagged it and looped it over his head before he followed Castiel who was waiting at the door for him.

"Let's go," he said and they made their way outside.

Cas loaded Dean into the back of the Impala. He was unconscious again and Sam wrapped him in a blanket, putting more underneath him because he knew Dean would never forgive him for letting him bleed all over his car. Then he drove out of the dilapidated part of town, looking for the nearest hospital. Castiel was very quiet in the seat next to him, continuously looking over the backseat at the wounded man.

"Something wrong, Cas?" Sam asked after a while.

The angel sighed. "It was my fault this happened to Dean."

"You were only following orders."

"I know," Castiel sighed. "But I should have protested the idea more. If I had noticed earlier everything that had been going on, that Alastair was nothing but a scapegoat…if he had killed Dean we all would have been lost, and I wouldn't have forgiven myself. Dean is my charge, Sam, both of you. And I turned my back for one instant and Alastair took him."

Sam was silent. He had blamed Cas initially for Dean's disappearance, sure, but getting to know the angel for the last couple days, he knew he felt bad enough about it already. Most of the angels were dicks, as Dean had said, but Castiel wasn't. In fact, after this, Sam definitely counted him as an ally. Maybe someday he would even be a friend.

"Look, Cas, we all make mistakes," Sam told the angel after a while. "I know it wasn't your fault, and I just want to thank you for helping me get Dean back, even though you could have gotten in trouble for it."

Castiel smiled wryly. "I probably will get in trouble for it, but I think they will listen to my case. I just wish I could have gotten the name of the angel responsible from Alastair."

"We'll find him," Sam said assuredly.

"In the meantime, do not leave Dean alone," Castiel said. "I fear this angel might try to kill him himself since Alastair failed."

Sam nodded, though he didn't like the thought at all, wishing this was over. "You're right. I'll look after him." He was silent for a moment then glanced over at the angel again. "Um, how're your wounds?"

"Healing…slowly," Castiel said with a shrug. "But I will be all right. You need to worry about Dean right now."

Dean moaned from the backseat and Sam glanced back at him, but he wasn't awake yet. He set his jaw, wishing almost that he hadn't killed Alastair so quickly. He knew that it wasn't just the physical pain that had put Dean into this state but the mental torture as well. He thought back to what Castiel had told him about Dean breaking the first seal and wondered, sickly, if Alastair had told him that, if he even knew. Sam swallowed hard and tried to force those thoughts from his head, continuing his search for a hospital.

Castiel carried Dean into the ER but as soon as they had gotten him on a gurney and were taking him in to the trauma ward, the angel turned to Sam.

"I need to go, I'm sorry, but I cannot delay any longer or I will risk them coming for me, and my case will be far harder to defend then."

"Yeah, of course," Sam said, holding out his hand. "Thanks, Cas."

The angel took his hand after only a moment's hesitation, still unfamiliar with the gesture. "I will be back if possible. Look after your brother. I…fear he will be in great distress when he wakes up."

Sam swallowed and nodded. "I know. I'll look after him."

Castiel nodded once and then was gone. Sam sighed deeply and looked to where Dean had been taken, before he was accosted by a nurse with paperwork.

"Excuse me, sir, can you please fill this out for your brother?"

Sam spent the next hour in the waiting room, anxious and restless, filling in their bogus insurance info and wondering how much longer they would be working on Dean. He had been a mess, sure, but Sam hadn't seen anything really too damaging. No surgery anyway, hopefully, just lots of stitches.

He got some coffee, even though he knew he didn't need any caffeine and when it was half drunk and long cold, the doctor finally came out to tell him he could see Dean. Sam hurried into the room the doctor showed him to and stopped halfway to the bed as he saw his big brother so pale and broken, his head turned away from Sam and his bare arms, the only part of his skin Sam could see, covered in bandages. He swallowed hard, his throat tight as he stepped forward slowly and pulled a chair over to Dean's bedside.

"Hey, Dean," he whispered, reaching up to put his hand gently on top of Dean's as it lay listlessly at his side. It still felt cold.

Dean's chest heaved once in a deep, hitching sigh before he turned his head to look up at his little brother, his eyes dull with pain and so much more that Sam's heart twisted in his chest as if someone had driven a knife into him.

"I'm sorry Sammy," Dean whispered, meeting his eyes with a look that told Sam he never expected forgiveness. "It's my fault. All of it. I broke… _everything_." And then he started sobbing, his damaged body jerking painfully with each heaving breath.

Sam felt tears slide down his own cheeks as he leaned over and carefully gathered his brother against his shoulder, cradling his broken body, unable to do anything else. He felt himself breaking with the horrible realization that Dean knew everything and he had no idea how he was going to come back from that.

Sam had already lost his brother once, how could he stand to lose him again?


	7. Chapter 7

**Hey, I hope everyone had a good Thanksgiving (if you celebrate it, that is ;) Here's another chapter for you. Again, some lines in this chapter were taken directly from "On the Head of a Pin". Also, there's only one chapter after this! I can't believe it's almost over, but I'm glad you guys have been enjoying it so far, thanks as always :)**

Chapter Seven

Sam was asleep when Castiel came back to the hospital, only allowing himself to rest his head on Dean's bed after his brother had exhausted himself with grief and finally slipped into sleep from the pain medicine. Sam looked so exhausted that Castiel couldn't bring himself to wake him, knowing he hadn't slept well in days, and instead took another chair on the opposite side of Dean's bed, sitting quietly, and thinking over everything that had happened.

He had gone back to heaven expecting a reprimanding, but instead found that no one had much time to spare for him. There had been another angel killed and it seemed that Castiel had not been taken off of the hunt for Dean after all. That was the most troubling thing; he hadn't actually been thanked for going after Dean regardless, but it seemed he hadn't been disobeying orders after all. And that made him suspicious, because he knew that narrowed the likely suspects down quite a bit. In fact there were only two likely angels that Castiel could bring to mind. One was Uriel, and the other, whoever had given him orders in the first place, or both of them together. Because it had always only been Uriel to relay the orders to Castiel about the hunt for Dean, and he had been one of the few who would have known the instant Castiel stepped out of the warehouse, not to mention that Uriel would have had time to speak to Alastair, and alone. He also had reason to want Dean dead. Not only because the elder Winchester had done nothing but needle at him since they met, but also that Alastair might have let slip his name—if it was indeed him—thinking it of little consequence if he was going to kill him anyway. While Dean had not been conscious long enough to ask yet, Castiel knew he needed to do so as soon as possible. Because whoever was responsible would likely be by to kill the hunter before he got the chance.

And that was why Castiel was there instead of looking for the killer with the rest of the angels. He had once again been put on duty to look after Dean, but the angels, never wanting to admit their own faults, were fools enough to think it was all over with the death of Alastair, when Castiel knew that to be the farthest from the truth. He could not voice his fears in front of the other angels though, because Uriel had been there the whole time, as well as anyone who might have related orders to him. Castiel's hands had been tied, but he was not going to let the traitor walk if he could help it, and he was certainly not going to let them kill Dean Winchester, not after saving him twice now.

Dean shifted on the bed then and moaned, and it was a testament to how deeply Sam was asleep that he didn't wake up, even at his brother's distress. Dean blinked at the younger man's sleeping head resting by his shoulder for a moment before he seemed to sense Castiel's presence and turned to look at him. Castiel sat up straight in the chair, leaning forward slightly, letting out a small sigh as he saw the look in Dean's eyes: anger, betrayal, and pain, and all directed at him.

"Are you…all right?" Castiel asked, knowing it probably wasn't the best thing to say, but he wasn't exactly used to what was proper in social environments.

Dean turned away from him to look straight ahead. "No thanks to you."

Castiel looked down at his hands, clasped in his lap. "It wasn't supposed to happen like that."

"Yeah, well, I appreciate the sentiment, but it doesn't do much good." Dean was silent for a long time and Castiel didn't know what to say either. Finally the hunter spoke again, his voice so quiet, the angel wasn't sure he was actually speaking. "Is it true?" Dean asked, turning to look at Castiel again. "Did I break the first seal? Did…did I start all this?"

Castiel couldn't meet his eyes, casting a glance over at Sam's sleeping figure. So Alastair had told him. His heart felt heavy at that, but he couldn't lie to the wounded man either. Not after everything that had happened. And it was inevitable he would find out eventually. He just wished it hadn't been when he was already hurting so badly. "Yes," he replied quietly. "When we discovered Lilith's plan for you, we laid siege to hell, and we fought our way to get to you—"

"So I started the apocalypse?" Dean cut in, his voice wavering with such emotion that it made Castiel feel even worse. The devastation on his face made the next truth even harder for the angel to get out.

"We were too late."

"Why didn't you just leave me there, then?" Dean demanded.

"It's not blame that falls on you, Dean," Castiel tried to assure him, but knew it did little good. "It's fate. The righteous man who begins it is the only one who can end it." He turned to him, hating even more what he had to say next. "You have to stop it."

Dean's body trembled at the enormity. "Lucifer? The apocalypse? What does that mean?" Castiel couldn't answer; he didn't have a good answer for that. He knew what it meant. Pain, suffering, worse than Dean had ever known before. "Hey," Dean demanded. "Don't you go disappearing on me, you son of a bitch; what does that mean?"

"I don't know," was all Castiel could say.

"Bull!"

"I don't," the angel insisted. "Dean, they don't tell me much. I know our fate rests with you. That's all."

"Then you guys are screwed," Dean said quietly, his voice shaking with emotion he was trying to fight back. "I can't do it, Cas, it's too big. Alastair was right, what he said. I'm not all here. I'm not—I'm not strong enough." Castiel watched helplessly as several tears slid down Dean's bruised cheeks. "I guess I'm not the man either of our dads' wanted me to be. Find someone else, it's not me."

"Dean," Castiel tried to say, but just then a stirring was heard and Sam sat up slowly, rubbing his eyes. He caught sight of Castiel then noticed Dean was awake, and lastly the fresh tears on the elder Winchester's cheeks.

"Hey," Sam said, putting a gentle hand on Dean's neck. "How are you?"

Dean took a shuddering breath. "What do you think?" he asked bitterly, then turned his head aside and closed his eyes again, allowing himself to slip back into sleep.

Sam just looked up and met Castiel's eyes with such pain in his own that the angel wished with all he had that he could simply release Dean from his duties. He knew it wasn't possible, that destiny had already been written, but, if he could have, he would have right then.

He talked to Sam a bit about what had happened and why he was there and not hunting the killer, all the while watching Dean sleep and trying to forget the devastation he had seen on the young man's face when he had confirmed his worst fears. He would probably never forget that.

Finally, as he saw Sam rubbing his head, which was likely aching from lack of sleep, not to mention the knock he had gotten earlier, Castiel realized he should be taking care of the younger brother as well.

"Sam, you should find something to eat, it's been since this morning."

Sam sighed tiredly, but nodded. "Yeah, I probably should. Can you watch him for a few minutes? I'm only going down to the cafeteria."

"Of course," Castiel replied, feeling somewhat glad that Sam trusted him enough to watch Dean. Especially after what had just happened.

Sam was gone for only a few minutes before a flapping was heard and Castiel felt a sudden presence in the room, getting up and looking toward the open door to find Uriel standing there.

"Castiel, I thought I would find you here. Though I was hoping not to."

"Uriel," Castiel said quietly, his mouth twisting with regret. "So it was you after all."

The other angel chuckled humorlessly, stepping into the room and closing the door behind him. Castiel moved to stand in front of Dean's bed, feeling the Winchester's bleary eyes on his back, awakened perhaps by instinct, and trying to process what was happening.

"Cas, what's going on?" he croaked. "He's the one who let Alastair out, isn't he? Aren't you, you dick—"

"Quiet, Dean, I'll handle this," Castiel told him, not looking away from Uriel, hoping Dean wouldn't make it worse. He shook his head sadly. "Why brother?"

"Why?" Uriel asked bitterly. "You have to ask? Why do you think, Castiel? Because our mission has turned from serving God to serving humanity. It is filthy work, acting as their servants. We are angels, we are above them."

"That's what Lucifer thought too, but he was wrong," Castiel told him. "You must see that."

Uriel chuckled again. "What I see, Castiel is a bunch of sheep serving filth. With the apocalypse, we have the chance to be put back into our rightful places, above the filth of humanity; it's where we belong."

"But it is out duty to protect them, Uriel," Castiel tried to tell him. "That was our purpose, our orders."

"From who? God? Why follow his word, you've never met the man, Castiel."

"It's called faith," Castiel told him firmly. "You saw that once, brother, what changed?"

"Too much," Uriel spat. "And you doubt too, Castiel, I know you do. Falling for humanity more every day; it's amazing you haven't been cast out already. And the worst is this pathetic mud-monkey that we must protect at all costs so he can stop the apocalypse." He gestured to Dean. "We lost good soldiers for him, and we will lose more before this is over and he can't even give us a humble thank you."

"So you would kill more of our brothers and sisters?" Castiel demanded. "Why, Uriel? To what purpose?"

"I only killed the ones who said no," Uriel said with a cruel smile playing over his lips.

Castiel frowned. "No to what?"

"Oh, Cas, so blinded by humanity that you can't see what's right in front of your face. To raise Lucifer, to start the apocalypse and put an end to it all, especially humanity."

Castiel's fists clenched, and he heard Dean curse under his breath. "So you tried to recruit angels from our garrison and _murdered_ those who told you no?" he demanded.

"Plenty said yes, Castiel. They're not all self-righteous little do-gooders like you. You'd be surprised how many angels want the apocalypse to happen. Some of us want our fallen brother back."

Castiel shook his head. "You are insane."

"No, Castiel. I am not, and I wish you could live to see that, but that is your choice." His angel blade slipped from his sleeve and he stepped forward. "I will bring on the apocalypse, and raise Lucifer, and to start, Dean Winchester must die. So step aside, Castiel, unless you want to join him."

Dean shifted in the bed, growling deep in his throat. "Back off you feathered douchebag."

Castiel didn't budge, only slipped the blade from his own sleeve. "I will not let you kill him, Uriel."

The other angel shook his head. "Then I'm afraid I have no other choice." He leapt forward and grabbed the front of Castiel's coat, flinging him against the far wall with a crack of plaster. Castiel was winded but got to his feet instantly, his blade raised as he struck out at Uriel before the other angel could get at Dean, hitting him with the hilt in the jaw. Uriel laughed, and grabbed the wrist of the hand Castiel was holding the dagger with, twisting until he was forced to drop the blade with a grunt of pain before throwing the smaller angel back to the ground and kicking him for good measure. He was still weak from his fight with Alastair and felt it even more as he was already tiring. Castiel rolled to a stop against Dean's bed and before he could gain his feet again, Uriel was on him, dragging him to his knees and slamming a fist into his face. Blood spattered onto the floor. He hit Castiel again and again until the angel slumped, gripping Uriel's arm just to stay upright as he spit blood onto the floor.

"You're pathetic, Castiel," Uriel said. "Why do you defend this human?"

"He's my charge," Castiel gritted out.

"You could join me, Castiel. Set our brother free, put an end to all of this. I would welcome you by my side."

"Are you trying to convert me, Uriel?" Castiel spat, trying to get to his feet, but Uriel wasn't allowing him to.

"I wanted you to join me, Castiel, truly, but I see you won't, not while your precious humans are in the way." He hauled him up bodily and threw him down, eliciting a yelp from Castiel as all his air was knocked from his already abused body. Uriel strode over to him, kicking him onto his back and pressing a foot against his neck to hold him down as he held his blade over him.

"There's still time for you to repent, Uriel, you don't have to do this," Castiel tried to say, struggling under the other angel's foot.

Uriel smiled at him. "I know I don't. But you see, I want to."

"Yeah, well, not today, asshat."

Uriel's face registered shock as an angel blade was shoved through his neck from behind. Castiel looked up to see Dean swaying on his feet, a look of pure determination on his face.

"Dean, get down, close your eyes," Castiel shouted and Dean fell to the ground and put a bandaged arm over his eyes as Uriel screamed in agony, his body glowing brighter before he exploded in a burst of light, leaving only a body and burned out shapes of wings across the floor and walls.

Castiel forced himself to his knees, crawling over to the fallen angel and retrieving his blade from his neck, before looking over at Dean who was trembling from the exertion and adrenaline rush. He met Castiel's eyes.

"Got tired of l-listening to h-him," he got out with a breathless chuckle. "H-how did you stand it?"

Castiel gained his feet and reached down to help Dean to his, lifting him up with a whimper escaping the Winchester as he was settled back onto the bed.

"Thank you," Castiel told him.

Dean shrugged. "Whatever, I figure I owe you." He almost fell forward but Castiel caught him by the shoulders and lowered him back against the pillows.

"Careful, you don't want to do Uriel's work for him."

Dean's eyes widened slightly. "Cas, was that a joke?"

The angel furrowed his brow. "I…didn't intend it to be humorous."

Dean rolled his eyes before he closed them, settling back with a pained sigh. "Yeah, well, at least you don't change." He cracked his eyes open again and looked around at the wing prints and Uriel's dead body. "This is going to be hard to explain to the hospital staff."


	8. Chapter 8

**Well everyone, this is the final chapter! Thanks so much to everyone who has followed and faved and reviewed this story you are all awesome and I always appreciate hearing what you have to say I'm very glad you've seemed to enjoy it ^_^ I hope you like the conclusion, and again, if you didn't get to read the prequel one-shot "When you Wake" this chapter kind of references it again a bit so if you want to see my version of how Cas got Dean out of hell, go check it out.**

Chapter Eight

Thankfully, Castiel was able to see to the mess before the hospital staff found out about it, putting a concealment on the burns so they would ignore them. Sam was frantic to find out that Dean had almost been killed while he was eating, and it took his older brother's tired assurances to calm him down.

Dean at least seemed to have been jarred back into some semblance of normal by the occurrence. Maybe it was the adrenaline, or maybe it was just acceptance, but he was quickly on the road to recovery, almost too quickly for his brother's liking. Sam had a feeling Dean was just doing what he normally did—suppress and ignore his problems until they culminated into a messy explosion. But there wasn't much he could do either. In a perfect world, Dean would admit that he had problems and they would work them out together, but that was never going to happen.

Two days later, Sam came up to his room after grabbing breakfast and coffee, to find him dressing himself in a pair of clean clothes he had found in the duffle Sam had brought into the room.

"Woah, Dean, where are you going?" Sam asked, hurrying over to his brother who was struggling to lift his arms enough to slip a t-shirt on. The younger man winced as he saw the strain it was putting on the deep lacerations on Dean's stomach and chest.

"Getting out of here," Dean told him in no uncertain terms. "I sure as hell ain't staying here any longer. I'm not dying, and even if I'm probably not hunting for at least another week, I can rest my wounds at Bobby's better without someone coming in and poking at me every half hour."

Sam set his mouth in a thin line, still unable to get the sight of his brother's broken body strapped to that table out of his head. "You lost a lot of blood."

"Which they replaced," Dean said matter-of-factly, grunting as he fought his arms into the t-shirt sleeves.

Sam finally decided to help him, knowing he wasn't going to succeed in stopping him. He helped Dean slip the shirt onto his arms and then eased it over his head.

"Look, man," Dean told him with a sigh, already so exhausted from putting clothes on that he had to sit on the edge of the bed. "None of this is going to get any better. You heard Cas, this is a crappy situation that I apparently don't have any say in. Not that I'm throwing in the towel yet, there's always some way to get around things in our experience. All I'm saying it, I just need to keep going, because I sure as hell am not going to sit around and feel sorry for myself."

Sam shook his head. "Yeah, I agree with that, but Dean, I need you to be honest with me: are you okay? I mean, the first seal aside, this thing with Alastair, I know it messed with your head. And not to be indelicate, but he tore you up; I know we get beat up on hunts, Dean, but torture like that? That wears on someone. It's not the same as getting injured on the job."

Dean looked up at him, resting his bandaged arms on his thighs. "You want the truth, Sammy? I'm as far from all right as it's possible to be. I mean, I started the _apocalypse_ ; I broke the damn world. That's not really something you can put a Band-Aid on, is it?"

"Dean," Sam said quietly, shaking his head.

"It's okay, I did it, I'll deal with it. You break, you buy, I know that," Dean told him. "And yeah, Alastair did a number on me, got into my head, but I'm not going to let that destroy me. You killed him; I don't have to worry about him anymore. The angel who was gunning for me is dead too. I call that a win. To be honest, I haven't been okay since I got back from hell anyway, so why should this bother me?"

Sam didn't know what to say. Sure, Dean wasn't catatonic and sobbing uncharacteristicly like he had when they found him, but he knew from experience that this, this devil-may-care suppression crap, was worse. He also knew that it was pointless to dig into it. In this case, with this new Dean, Sam was afraid he might push a button that could cause him to have some psychotic break. Maybe Dean wasn't that broken, at least Sam fervently hoped not, but he wasn't going to take the chance either. He knew from experience that Dean would talk about his feelings when he was good and ready and trying to do so before was only going to make him clam up. At least he was functioning.

Sam sighed and nodded. "Okay then, I guess I'll go get the nurse to sign your release papers." He was about to leave when he turned back around, reaching inside his collar. "Oh, by the way, I forgot to give this back to you." He pulled the amulet from around his neck and dropped it into Dean's hand.

Dean looked at it for a long moment, before he nodded, meeting Sam's eyes as he looped it over his head, his hand clutched around it as it rested against his chest. "Thanks Sammy."

Sam nodded then turned quickly before the prickling that had cropped up in his eyes at Dean's expression turned into more, and hurried from the room.

As soon as his little brother left the room, Dean slumped, his elbows on his knees and his head in his hands. No, he was anything but okay, but he wasn't going to admit that. Not to Sam and especially not to himself. Because if he admitted how broken he really was he knew he would never have the strength to get up in the morning and he didn't get that luxury. Not while he had a world to save. Not while Sammy still breathed. This had all started because of Dean, and he wasn't going to let it ruin his brother too. It was his fault, and he would pay the price himself because that was what he did and that was what he would continue to do until there was no longer breath in his body, and he didn't get to whine about it.

He sighed deeply and stood, forcing his aching body upright as he packed his bag up again, waiting for Sam to get back. As he was going through the bag, he found his flask and quickly opened it, swallowing half the contents in one go. He closed his eyes and let the alcohol burn its way through his system. He put the flask away and looked down at his hand, shaking and unsteady and clenched it until he forced it to be still.

Because he wasn't okay. At all. Hell, Alastair, the task ahead of him; he knew if he thought about it too much he wouldn't be functioning at all. Of course that didn't help the nightmares any. He didn't know what he was going to do, but he knew he had to beat it someway. Because in truth, he knew he couldn't stay in the hospital any longer, because if he did, he was afraid he would never leave.

* * *

 _Several days later_ Dean was out working on the Impala in Bobby's yard, having had enough of being cooped up inside. His injuries still hurt and he wasn't sleeping, but this was all the therapy he needed. That and the bottle of whisky that was resting inside his toolbox. Thinking about it, he set his wrench aside, and wiped his hands on a greasy rag before taking up the bottle and taking a burning swig of it. His hand shook slightly as he put it down and he wiped his brow, taking a deep breath.

He couldn't get Alastair out of his head, not to mention thoughts of the impossible task ahead of him. He didn't like being in the spotlight, he didn't like being noticed at all. In his line of work, it was best to stay low key, but he liked the anonymity, it made it easier. And now what? He was being chosen by God to stop the apocalypse? No one could blame him for being unable to wrap his head around that. Why him? He wasn't righteous, he was broken, and on top of it all, he was scared as hell. He knew he didn't have the edge he used to, not since he had come back from the pit. And what was worse, he knew that Sam saw it too. The way he looked at him with something that was somewhere between sadness and pity and pain made Dean feel sick because he knew he wasn't all right, and if he wasn't all right, and Sam saw it, how was he supposed to keep anything from happening to his brother? Because if he was fighting someone else's war, where did Sam fit into it? He didn't trust the angels at all; he at least had enough instinct left to know that, not after what had happened with Uriel. If one had turned and had followers who wanted the apocalypse, how many others were there who wanted the same thing? Ones who were willing to do more than simply kill Dean; they might try to use Sam as leverage, and if that happened, they could kiss their righteous man goodbye, because Dean wasn't going to get in with any of them then. He would take Sam away and hole up until the whole world ended for all he cared, but he wasn't going to let them take away his family. Especially not after everything they had already been through just to get to this point.

The thought of everything that was expected of him made the flutter of panic rise inside his chest. This was new too, he had never been scared like he had after hell and it wasn't pleasant, but there was nothing he could do about it. The lack of control, over his own body too, made him angry. He was done with this. He threw the wrench he was using back into the toolbox and then slung the whole thing along with the bottle of whisky to one side, ignoring the pain that ripped through his body at the sudden movement as he turned to lean against the bumper of the Impala, breathing heavily.

"Dean."

He spun around with a bit off shout, seeing Castiel standing there, in his usual rumpled state, his typical blank look holding just a tiny frown of concern.

"Damn it Cas," he grumbled, trying to hide the fact that he was shaking. "Give a guy some warning."

Cas bobbed his head apologetically. "I didn't mean to startle you."

"What are you doing here?" Dean demanded. "Did you come to take me away on another mission? Maybe act as torturer for you again?" He knew it was harsh, especially after Sam explained to him how Cas had pretty much defied orders to go look for him when he had been taken by Alastair, but he was still bitter, and his body ached, and he had even more nightmares than before, so he felt inclined to a little surliness at least. However, he instantly felt bad when he saw the pained look enter the angel's face. This was new, this slight show of emotions that Cas was beginning to allow.

"I will never forgive myself for what happened with Alastair and Uriel, Dean," he said. "But you have to understand that I am expected to obey my orders so things can run smoothly. There is so much rebellion right now with angels defecting to Lucifer's side, that we cannot afford disobedience."

Dean lowered himself to sit down on the Impala's hood. "I get it, really I do. I always followed my dad's orders, sometimes maybe when I should have used my better judgment. But Sam explained to me later that that wasn't always the best thing to do, and sometimes you have to break a few rules. It doesn't mean you respect the person giving them any less, it just means that sometimes people can't always see what the right thing to do is, and someone else has to step in and decide that for them."

Castiel gave a small wry smile. "We do not all have that luxury, Dean, but I do think I understand what you are talking about now. And, against my better judgment, I have begun to see why Anna left in the first place."

Dean looked up at the angel then, and fully appreciated what he had been through in the past week, the decisions he had to make in order to make sure Dean was safe. Sure, it was mostly because he was useful to him and the war that was coming, but Dean also felt an inexplicable trust toward the angel, and he didn't think that was without cause. He cleared his throat, slightly self-conscious about what he had to say next, but figuring it would be something Sam would say. "By the way, I'm sorry about what happened with Uriel. I mean, sure, the dude was a dick, but he was your brother in arms, and I know how hard it is to have someone turn on you like that." Okay maybe he had to work on being a little more eloquent with his empathy, but it was a start.

Castiel nodded with a small sigh. "I should have seen it coming, truthfully. I will not allow myself to be so blinded again. Now that I know these betrayals are happening, I will be more cautious in who I trust."

"I guess no one is really who they say they are," Dean commented.

Castiel looked straight at him then with that dorky head-tilt. "You are, Dean."

The hunter snorted at that but Castiel continued. "You are perhaps one of the most honest men I have come across. You know who you are and what you want, even after everything that has happened to you. You may pretend otherwise, but there is a reason you were the righteous man."

"Yeah, about that," Dean said. "I still don't get why you saved me. I just don't buy the part about me being the only one to stop the apocalypse."

Castiel gave him an odd look as if he was trying to remember something from long ago that wasn't quite there anymore. He shook his head slightly before he replied. "I think myself, and some others simply saw that you were worth saving."

"I _broke_ , Cas!" Dean shouted suddenly, surging to his feet and taking a step toward the angel. He was still furious at himself, disgusted. He hadn't coped with it before and spending several days being taunted by Alastair had just brought everything back full force. "I got off the rack, and I took his blade and started carving souls apart. And the thing was, Cas, it was easy. It was easy to give back the pain I had suffered, it made me forget all the other crap I had to deal with. So how is that in any way good or righteous?"

Castiel shook his head. "But you were miserable, Dean. You may have tricked yourself into thinking it was easy, but you didn't really believe that. Otherwise, why would it bother you so much now?"

"How can you be sure?"

Castiel opened his mouth, but hesitated, then finally said. "I just know that isn't you, Dean."

Dean looked at him for a while, then voiced something that he had been wondering, something he had been wracking his brain about. "Do you remember rescuing me? Because I don't remember a damn thing. I remember everything else but not that. How come I don't remember that?"

Castiel shifted slightly, frowning again. "It's a blur, but I remember finding you and taking you out. But you were probably not meant to remember."

Dean shrugged, siting back down on the hood of the Impala, wincing as several of his wounds pulled again. He was trying to remember anything he could, but the only thing that happened was a small tingling feeling over the scar Cas had left on his shoulder. He refrained from touching it but again felt _safe_ with Cas, _protected_. Those were the words that ran through his head. Odd after everything that had happened, but Cas seemed different now, not as stiff, not as hard. Maybe going after him in hell had done something to him too. But still, Dean wasn't inclined to trust without proof, and he looked up to meet the angel's gaze.

"I need to know something Cas, and I want you to be truthful with me," he said.

"Of course, Dean," the angel replied.

"You're at my back on this whole thing, aren't you?" the hunter asked. "I mean, I can trust you, right?"

"Of course, Dean," there was almost a little hurt in Castiel's voice as his brow furrowed. "You are my charge, and I have always looked after you. That is, first and foremost, my job."

Dean felt a little better at hearing that. "I need you to promise me something then," he said. "If things go to crap, and they probably will before this is all over, can you make sure, no matter what happens to me, that Sammy is taken care of? I don't like the way the angels look at him, but… you don't look at him like that, and I think I can trust you, but I need to make sure he's gonna be okay if I don't make it out of this. No one's getting my help otherwise."

Castiel gave him what could only be described as a fond look before he turned serious again. "I will make sure Sam is safe, Dean."

"Thanks, Cas," Dean said, feeling slightly relieved. He turned to pick up the tools he had thrown and the bottle of whisky, looking at it for a long moment before he set it aside again, swallowing hard. It didn't really work anyway. His problems were far beyond drinking away.

"Dean," Castiel asked softly and the hunter turned back around to look at him. "You really don't remember anything about getting out of hell?"

Dean shook his head. "No."

"Oh," Castiel looked down.

"Why, should I?"

"No," the angel shook himself. "I was just wondering, because I feel like I should remember it, but I only remember the fight in and the fight out. It's just that Alastair seemed upset at me like we had met down there, and I couldn't remember it with any clarity."

"Hell does weird things to your head," Dean told him. "I'm sure you had other things on your mind."

Castiel nodded. "I suppose it's not entirely important anyway. How are you feeling by the way, Dean?"

Dean looked down for a minute before fixing his typical smile on his face. "Just peachy, Cas."

The angel frowned, but chose to ignore him as he realized that is what Dean wanted. "Rest up while you can. I think you will be needed before long. But remember, Dean, you _can_ trust me."

Dean nodded slightly. "Yeah, I guess I can. Um, I know I didn't say it before, but thanks for helping Sam get me out. I'm afraid he would have been killed without you."

"As you said, we're even," Castiel replied with a small smile. "I must go now, I have some duties to see to."

"Yeah, of course," Dean said, and the angel disappeared in a flap of wings. Dean sat there for another long minute, and finally picked up the bottle of whisky again, taking a long swing of it. It was going to take a lot more before he was able to think about the task ahead.

* * *

 **And that's it. Thanks again so much! I have a few more things in the works that you might see within the next couple weeks. In the meantime, I had really wanted to do some Christmas stories but really have no real ideas so I thought that instead I would do a series of request one-shots, so if you guys have any Christmas story ideas involving our boys please let me know! Anything goes (though no slash as always) just try to keep the plots from being too elaborate, please I'm going to try to keep them 3,000 words tops so I'll have time to write all the requests. But please either PM me or leave a request in the comments :)**


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